| Friends of Car-Free Key West & Duval Street/Historic Downtown

A Solution in Search of a Problem: Why the Simonton/Angela Street Garage Doesn’t Add Up

Posted on January 31, 2026 Leave a Comment

Before You Build, You Measure: The Data and Planning Gaps Behind a $6M Garage

The January 27 public workshop on the proposed parking garage that will net 89 new spaces at Fire Station #2 was billed as a “listening session,” but it played more like an attempt to justify a project in search of a rationale. About 25 residents attended, along with the Mayor, several commissioners, and a noticeable line of City staff along the back wall. What unfolded was not a data‑driven case for a major capital investment, but a series of broad claims that the garage would somehow satisfy all four of the City’s strategic goals—without offering meaningful evidence to back any of them up.

Staff insisted the garage would advance infrastructure, affordable housing, sustainability/environmental adaptation, and financial stability. Yet no data was presented to demonstrate demand for a garage, no inventory of public and private parking in Old Town was offered, and no analysis was provided to show how this project fits into a broader transportation strategy. As one resident bluntly put it: “All you think about is parking because you are parking guys. I hope the commissioners are looking at the whole of transportation.” It was clear the presenters were not.

Instead, the meeting leaned heavily on the idea that this project “checks all the boxes” and can be started quickly—hardly a justification for a multimillion‑dollar structure in a flood‑prone neighborhood with longstanding safety concerns. The City never fully articulated why this garage is needed, why this location is the right one – other than it’s the easy one, or how it meaningfully advances the community’s long‑term mobility goals.

In the sections below, we examine why the City’s four‑strategic-plan goals argument doesn’t hold up. We explore the missing data including a parking demand study, inventory of existing parking supply and the overall transportation context. We’ll highlight the concerns raised by residents—along with the City’s lack of substantive answers. In earlier articles here and here, we left open the possibility that a well‑justified garage could be a win‑win for Key West. But after this meeting, it’s clear the City has not made a convincing case. Until they do, this project should not move forward.

*At left City Parking Director John Wilkins addresses audience. At right, the audience a few minutes in.*

The City’s “Four Strategic Goals” Argument — And Why It Doesn’t Hold Up

During the presentation, both John Wilkins and City Manager Brian Barroso repeatedly emphasized that the Simonton & Angela garage “beautifully” satisfies all four of the City’s strategic planning goals: infrastructure, financial stability, sustainability/environmental adaptation, and affordable housing. It was the central pillar of their pitch — the idea that this single project neatly aligns with the City’s highest priorities. Yet even a cursory look at the details shows that this is a generous interpretation at best. And while the City’s website lists a slightly different set of strategic priorities for 2024–2025, we’ll take the four goals presented at the meeting as the operative framework. Even on those terms, the case simply doesn’t hold.

1. Sustainability / Environmental Adaptation

It’s hard to imagine anyone genuinely associating sustainability or environmental adaptation with a parking garage. On its face, the claim is absurd. Adding EV chargers is absolutely the right thing to do — but it doesn’t make it a sustainable project. It’s also the easiest box to check, and in this context, it functions more like lipstick on a pig than a meaningful climate strategy. A garage is, by definition, an invitation for more cars to drive into Old Town, not fewer. That alone puts it at odds with any serious sustainability goal. Adding reliable and frequent transit or safer bike lanes – now that’s meeting the goal, but we digress.

Staff also leaned on the idea that the garage would reduce “circling,” but we debunked that thoroughly in our recent Doris Day parking article. The real cause of circling isn’t a lack of structured parking — it’s the illusive free and underpriced on‑street spaces that drivers hunt for like George Costanza searching for the mythical perfect free spot. Until the City addresses that underlying incentive those free spaces pose, a new garage won’t meaningfully change driving patterns or reduce emissions.

*Doris Day ALWAYS found a parking spot right in front of her destination. Something that happens a lot in movies but not in real life or in any thriving downtown.*

2. Affordable Housing

The City’s attempt to link the garage to affordable housing rests entirely on the “third dollar” mechanism — the idea that every additional parking transaction generates a small contribution to the housing fund (33 cents of the third dollar collected for each $6 an hour transaction). That’s fine as far as it goes, but it’s a revenue argument, not a housing argument. Nothing about a parking garage meaningfully advances housing affordability in Key West. It doesn’t create units, preserve existing housing, or reduce costs for workers. It simply assumes that more cars driving into Old Town will produce more transactions, which will produce more dollars, which will eventually trickle into the housing budget.

What was missing was any explanation of scale or impact. How much revenue would the garage realistically generate after you factor in the deeply discounted employee parking permits? How much of that would actually reach the housing fund? And what would that amount accomplish in this market? Staff offered no specific numbers, no projections, and no context for the housing money. Without that, the affordable housing justification feels like an afterthought — a convenient talking point rather than a meaningful policy connection.

If they really wanted to address affordable housing they should have proposed building units on top of the garage, like the proposed garage on Stock Island. That, we would have liked, even if we’d need to scuttle the height limit to do so.

3. Financial Stability

The financial stability argument was presented as one of the strongest justifications for the garage, but it quickly fell apart under even modest scrutiny. Staff projected roughly $400,000 a year in “new” revenue would go into transit, affordable housing and every part of the budget. They emphasized that visitors — not residents — pay 85% of parking fees. On the surface, it sounds good that there’s more money and reassuring that someone else is paying for it. But without a demand study, an inventory of existing parking, or any analysis of utilization patterns, these numbers amount to little more than hopeful arithmetic.

The City is essentially assuming that if it builds a garage, the cars will come. Or would they be cannibalizing from other lots and thus be revenue neutral. Yet they offered no evidence that Old Town suffers from a shortage of parking – other than paid parking is expensive therefore it must be scarce, no data on how often existing lots fill, and no explanation of how discounted employee parking permits — which they also highlighted every chance they could get as ample justification for the project — would affect revenue as those people would be paying $30 a month for a space not $6 an hour. A $6 million capital project amortized over 15 years (City Manager) requires more than optimistic projections; it requires a clear understanding of demand, pricing, and behavior. None of that was presented.

There’s also a political dimension the City didn’t address. If the garage underperforms, residents will inevitably shoulder the burden through higher fees or redirected funds. Framing the garage as a financial win for the City without presenting the underlying assumptions is not transparency — it’s wishful thinking dressed up as fiscal prudence.

4. Infrastructure

Of the four strategic goals, infrastructure is the only one the garage clearly satisfies — but even here, the City’s argument was surprisingly shallow. Staff leaned heavily on the idea that this is the one capital project they can “start within 11 months,” as if speed alone were a justification. Being shovel‑ready is not the same as being strategically necessary. A project can be easy to build and still be the wrong project.

What was missing was any explanation of why a garage, at this location, at this moment, represents the highest and best use of infrastructure dollars. The City dismissed the Stock Island alternative without presenting a transparent comparison, even though a mobility‑focused facility there could support a broader transportation strategy rather than funneling more cars into Old Town. They also dismissed the City lots at the Seaport because of the aesthetically pleasing view.

And there was no discussion of opportunity cost — what other infrastructure needs, such as protected bike lanes, transit buses, repaving of streets and wider sidewalks in and around our main street, might be delayed or displaced by committing $6 million to a garage? The City Manager numerous times mentioned the need for a pump or lift station as the first part of the Duval Street Resiliency Project and that they were going to Tallahassee to get money for it because it was so important. If infrastructure is truly the goal, the City owes the public a clearer rationale than “we can build it quickly.” Infrastructure should solve a problem, not simply fill a timeline.

Is there really a need for parking or does everyone just perceive that because they want “Doris Day Parking”? We might have a better idea if the City provided a demand study, parking inventory study and transportation context.

The Missing Pieces: Demand, Data, Context and Mitigation

A. No Demand Study

At the meeting, Chris Massicotte — president of Keys Last Stand and a current candidate for City Commission — asked staff directly whether a demand study exists. They acknowledged, plainly, that it does not. For a $6 million capital project whose justification hinges on parking demand, that absence is astonishing.

A demand study is the foundation of any responsible parking investment — the basic homework that precedes design, location, financing, and policy decisions. Until the City can demonstrate actual need with real data, the project shouldn’t advance beyond the conceptual stage.

B. No Inventory of Existing Parking

Just as striking as the absence of a demand study is the fact that the City has no inventory of existing parking. Staff offered no data on how many public off and on-street spaces currently exist, how many private lots/spaces operate in Old Town, how often they fill, or what utilization looks like during peak and off‑peak times of day or seasons. Without that baseline, it’s impossible to know whether Old Town is actually short on parking or whether the issue is simply one of pricing, distribution, or management – and we’ve written about the need for better managing demand extensively here, here, here, here and here).

A parking garage is supposed to solve a defined problem. But the City hasn’t demonstrated what the problem is, where it occurs, or how big it might be. Building new supply without understanding existing supply is planning in the dark. Before committing millions to new construction, the City should be able to answer the most basic questions: How many spaces do we have? How are they used? And what specific gap are we trying to fill?

*The City has adopted Bike/Ped (left) and Transit Plans. Why not a transportation plan that covers everything?*

C. No Transportation Context

Perhaps the most revealing gap in the entire presentation was the absence of any transportation context. A parking garage is, fundamentally, a transportation intervention — it shapes how people move, where they go, and what modes the City prioritizes. Yet staff offered no discussion of how this garage fits into Key West’s broader mobility goals, no analysis of travel patterns, and no consideration of how it interacts with transit, biking, walking, or the island’s constrained street network.

Without that context, the garage exists in a vacuum. The City didn’t explain whether it expects more cars to enter Old Town, how those cars will affect congestion, or whether the garage supports or undermines long‑term goals around reducing vehicle dependence. They didn’t address the role of employee parking, visitor turnover, or the well‑documented mismatch between free on‑street parking and paid off‑street supply. In short, they presented a transportation project without a transportation plan to support it.

A responsible mobility strategy starts with understanding how people move today and how the City wants them to move tomorrow. None of that was part of the conversation. And without it, the garage is not a solution — it’s simply an assumption.

D. No Mitigation

In our article of a couple weeks ago we suggested that should the City proceed, at minimum it should provide some mitigation or accommodations to help the garage pill to go down. Those included: dedicating all the new revenue to transit; committing to restarting a free Duval Loop; removing a few parking spaces from nearby retail streets for wider sidewalks/or parklets and bike infrastructure; eliminating nearby free on-street parking, improving wayfinding to all the garages and lots – public and private, and committing to a downtown multi-modal transportation plan. Without these items the garage is simply a sop to car drivers and nobody else.

Staff claim that a garage will reduce circling for parking and that reduces congestion. But research shows that like George Costanza, people will try to find those free parking spaces – and there’s well over 1,000 unmarked, free for up to 72 hours of them, rather than park in a garage and THAT’S what really causes congestion. So until the City addresses this, it undercuts the garage.

The Public’s Concerns

If the City expected the workshop to generate enthusiasm for the garage, the public response, with a couple exceptions by business owners looking for employee parking, told a very different story. The people who showed up — business owners, neighborhood residents, civic leaders, and even most of the commissioners — raised concerns that were consistent, substantive, and rooted in lived experience. And it’s worth noting: this was only a fraction of the community. Many voices who share these worries weren’t in the room, but the themes were unmistakable.

Flooding and Site Conditions

One of the clearest messages came from Kate Miano, owner of The Gardens Hotel, who both spoke at the meeting and submitted a detailed letter to the Commission. She described the chronic flooding on Angela Street — not during hurricanes, but after any rain event. Since the fire station and its elevated parking were built, stormwater now cascades down onto Angela like a waterfall. The proposed garage would rely on that same street for all ingress and egress. As she put it, the entrance to a multimillion‑dollar garage cannot be “simply not usable if it rains.”

Her broader point was equally sharp: Key West should be reducing car dependence, not building infrastructure that induces more driving in the historic district.

Congestion, Traffic Flow, and Induced Demand

Residents echoed similar concerns. Old Town already struggles with congestion, and many noted that adding more parking downtown doesn’t solve that problem — it worsens it. Several pointed out that workers increasingly rely on e‑bikes, scooters, rideshare, and transit, and that the City should be supporting those modes rather than doubling down on cars.

Fiscal Concerns and Taxpayer Impact

Commissioner Sam Kaufman, who attended the workshop, posted his own summary afterward. He highlighted a point that never surfaced in the staff presentation: the likely tax impact. Based on standard financing assumptions, a $6 million garage could translate into a 2–3% property tax increase. That burden would fall hardest on small businesses and renters, who already face rising costs and could see higher rents as taxes are passed through.

He also questioned why a downtown garage is being treated as a top priority when flooding mitigation and other critical infrastructure needs remain unaddressed.

Lack of a Transportation Plan

Kaufman’s post also underscored a theme that ran through the entire meeting: the absence of a transportation or transit plan. Residents and business owners repeatedly asked how the garage fits into the City’s mobility goals. No clear answer was offered.

A Call for Thoughtful Planning

Despite the frustration, the tone of the room was constructive. People thanked staff for their professionalism. They asked for data, context, and transparency. They asked the City to read its own studies — including the Stock Island Intermodal Center plan, which many believe offers a more strategic, long‑term solution.

The message was simple: Key West deserves thoughtful planning, not a rushed project that creates more problems than it solves.

*The City’s Stock Island Garage study provides 255 parking spaces AND workforce housing on top.*

A Project in Search of a Problem

Taken together, the City’s presentation, the missing data, and the public’s testimony all point to the same conclusion: the Simonton/Angela Street garage is a project in search of a problem. The City has not demonstrated demand, has not inventoried existing supply, and has not placed the proposal within any coherent transportation strategy. Instead, the justification rests on convenience — it’s “shovel‑ready,” it fits a timeline, and it’s something the City knows how to build.

But infrastructure should solve a real need, not simply fill a calendar.

The public understood this immediately. Residents spoke about flooding, congestion, and neighborhood character. Business owners raised concerns about induced demand and the long‑term consequences of doubling down on cars in Old Town.

Even more telling: the City already has a study outlining a more strategic, long‑term solution — the Stock Island Intermodal Center — which aligns with mobility goals, supports workforce housing, and reduces congestion downtown. That study was barely acknowledged other than to disparage it because of the transit department’s inability to provide reliable funding for service – this from their own staff – not us.

In the end, the January workshop didn’t build a case for the garage. It confirmed what many have been saying for months: Key West deserves a transportation plan, not a parking project. A city that prides itself on sustainability, historic preservation, and livability should not be rushing into a $6 million garage without the data, context, or vision to justify it.

Key West deserves thoughtful planning, not a rushed project that creates more problems than it solves. If the City meant what it said about listening to the community, then the public’s concerns should matter more than the convenience of a shovel‑ready project.

# # #

Note: You can watch the hour and 20-minute meeting here on YouTube.

Chris Hamilton is the founder of Friends of Car-Free Key West & Duval Street/Historic Downtown, a local advocacy group championing sustainable mobility and vibrant public spaces. Subscribe to the blog and follow on Facebook, Twitter, and Substack for updates. All stories are cross posted at KONK Life News. Originally from Washington, D.C., Chris spent over two decades leading nationally acclaimed initiatives in transit, biking, walking, and smart growth for Arlington County, VA’s DOT. Since moving to Key West in 2015, he has embraced a car-free lifestyle downtown, dedicating his time to non-profits and community projects. Explore all Streets for People column articles here.

Does a Stock Island Garage Makes More Sense Than One Downtown?

Posted on January 24, 2026 1 Comment

There’s Already a Fully Developed Study that Shows the Stock Island Intermodal Center Could Alleviate Downtown Parking Shortages, Reduce Congestion, and Support Affordable Housing

While Key West officials are meeting on January 27 to discuss plans for a new parking garage at Simonton and Angela Streets, adding 85 net new spaces downtown, a much larger and more ambitious parking garage proposal on Stock Island has quietly evolved into a fully developed project. It’s called the Key West Intermodal Center (KWIC), a multimodal transit hub that integrates parking, workforce housing, commercial space, and transit connections.

The Stock Island garage concept has been referenced in the Key West Transit Development Plans since 2020, including a detailed mention in the FY2025–2034 plan, which highlighted a “Key West Intermodal Facility Study.” That study is complete and it concludes with staff enthusiastically saying that “developing a multi-modal transit facility – including housing, parking and commercial space is achievable at Key West Transit’s current location” on Stock Island. City staff are already outlining next steps.

This new information transforms the narrative: the Stock Island garage is no longer a vague idea, often bandied about on social media, but a strategic, multifaceted project actively moving through planning and feasibility phases. It begs the question: Why aren’t we talking about it? Because if we can get the parking right, along with fixing our transit, it will make our historic downtown core more pedestrian friendly, less like mainland places – and that’s better for business, visitors and all of us local residents and workers too.

So, in our story below, we do just that. We dive into the details of what’s in the “Key West Intermodal Facility Study” and explore what this may mean for our island and the downtown Simonton and Angela garage discussion. Let’s go:

What the Feasibility Study Reveals

The impressive Key West Intermodal Facility Study (110-page Study and PowerPoint summary presentation) offers a comprehensive evaluation of the Stock Island garage proposal. It examines alternative locations for a hub garage, land use, traffic impacts, financial viability, and community needs, positioning the project as a strategic park-and-ride hub designed to intercept vehicles before they reach downtown Key West.

As part of the process, the study was vetted by city staff, transit officials, and community stakeholders, reflecting a collaborative process that aligns with broader city goals such as reducing carbon emissions, improving transit accessibility, supporting workforce housing, and enhancing community amenities.

Key features of the Key West Intermodal Center (KWIC) project include:

A public parking garage designed to reduce downtown congestion by encouraging transit use.
On-site affordable workforce housing for transit employees and possibly others.
Commercial and retail spaces such as cafes and convenience stores and community space.
Green spaces, public electric vehicle charging stations and bicycle infrastructure.
Enhanced transit connections, including shuttles and fixed-route services to downtown.

As part of a Title VI process, the study evaluated three different locations:

at 14^th and Glenn Archer Jr. Streets;
3215 N. Roosevelt Boulevard; and
5701 College Road (the current transit facility property).

*Left the study looked at 3 sites. The two others: 14th & Glenn Archer Jr. Streets and 3215 N. Roosevelt Boulevard at right.*

It concluded the current transit site best met the Title VI requirements and offers “exemplary” connectivity with existing transportation networks and says the site offers the best flexibility.

Once a site was chosen, the study then evaluated three development scenarios on the College Road location, each balancing risk and benefits:

Option A: Conch Community Hub – Mixed-use with commercial (5,500 sf of cafes & restaurants), community spaces (3,00 sf), and affordable housing (36 units) over parking (255 spaces).
Option B: Stock Island Live, Work, Play – Housing (54 units) for transit employees and others, with commercial (6,000 sf) amenities like cafes and convenience stores, community space (6,000 sf) over parking (255 spaces).
Option C: Heron Transfer Hub – The lowest risk option focusing on parking (255 spaces) and housing for transit employees (18 units) with a 2,500 sf community space.

*Renderings of the three scenarios. Options A and C show here and Option B shown at the top of the story.*

The study concludes that developing a multimodal transit facility at the current Key West Transit location is achievable and aligns with the city’s strategic priorities. It emphasizes the potential to alleviate downtown parking shortages and congestion while supporting affordable workforce housing and enhancing community amenities.

Current Status and Next Steps

According to a memo from Rogelio Hernandez, Key West’s Transportation Director, the feasibility study supports moving forward and outlines several preliminary steps:

Conducting market research, traffic analysis, and financial planning.
Identifying necessary road improvements on College Road.
Establishing a financial plan for the project.
Rezoning the site for residential and commercial use.
Securing variances related to building density, height, and parking requirements.

*The Stock Island Garage seems to fulfill more needs than the Simonton/Angela Garage*

Comparing Stock Island and Simonton/Angela Garages

The Stock Island garage represents a strategic park-and-ride approach aimed at reducing downtown traffic by intercepting vehicles earlier and promoting transit use. This approach is supported by data* showing that of the roughly 2.07 million overnight visitors to the Florida Keys who stay in Key West annually, approximately 66% arrive by car—about 1.37 million people. These figures are based on the Monroe County Tourist Development Council Visitor Profile Study and Key West tourism statistics, which track visitor demographics and transportation modes.

Capturing a significant portion of these vehicles at the Key West Intermodal Center (KWIC) before they reach the island could substantially reduce downtown congestion and parking demand.

The Stock Island project is part of a broader vision to integrate housing, commercial space, and green amenities, creating a multimodal hub that supports sustainable urban mobility.

In contrast, the Simonton and Angela garage is a smaller, more immediate project located within the downtown area, focused on adding 85 net new parking spaces where demand is already high.

While the downtown garage purports to address immediate capacity needs, we’ve discussed the ways it comes up short (Should Key West Be Building Another Downtown Parking Garage? January 17, 2025). The Stock Island project offers a longer-term, more comprehensive solution aligned with sustainability and mobility goals.

Caveat: Is the Stock Island Proposal Even Big Enough?

Given all those visitors and workers who arrive by car annually, a 255-space garage would seem to only accommodate a fraction of that volume, although that’s a lot more than the 85 new ones downtown. But it does raise a question: Is the proposed size sufficient to make a meaningful dent in downtown congestion? Or should the project consider a larger facility on that site, perhaps eschewing the housing, or also build additional Stock Island or New Town facilities (such as the other sites in New Town that were evaluated in the study on pages 24 – 32) and/or complementary strategies, like better parking management downtown to truly address parking and traffic challenges? We think people should be considering all of this.

*Within hours of publishing this story we received this comment on Facebook and love it. Since the Study looked at two sites near Searstown in addition to Stock Island, why not try this out?*

*Renderings of the Proposed Parking Garage on Simonton and Angela Streets.*

Why the Stock Island Idea Matters Now

The Stock Island Intermodal Center (KWIC) proposal is especially timely given that approximately 1.37 million of the roughly 2.07 million annual overnight visitors to Key West arrive by car. And as we’ve documented in other articles, as more and more of us live up the Keys because of housing affordability issues on the island, it means more of us are forced to drive to work. Capturing a significant portion of these vehicles before they reach downtown could dramatically reduce congestion and parking demand, while making our downtown core more pedestrian and bike friendly.

Beyond visitor and worker traffic, the project supports broader city goals including affordable workforce housing, carbon footprint reduction, and enhanced community amenities. By encouraging alternatives to driving downtown, the Stock Island garage balances convenience with sustainability, offering a comprehensive solution to Key West’s mobility and housing challenges.

With a public meeting on January 27 about the Simonton and Angela garage, the results of the Key West Intermodal Feasibility Study could reshape the conversation. Residents and stakeholders should watch for:

Any commission discussions of the Stock Island Study.
Public outreach and feedback opportunities.
How the city plans to integrate and/or prioritize these two projects.
Potential impacts on zoning, funding, and construction timelines.

This evolving story highlights the complexity of addressing parking and transit challenges in Key West. The Stock Island Intermodal Center offers a bold vision that could redefine how the city manages mobility, housing, and sustainability for years to come.

Stay tuned as we continue to follow this important conversation about Key West’s transportation future. Because if we can get parking and transit right, we can make the pedestrian experience in our downtown core even better – and that’s good for all of us.

# # #

*Sources and Methodology

The visitor and transportation mode data cited in this article are drawn primarily from the Monroe County Tourist Development Council (TDC) Visitor Profile Study (2024) and Key West tourism statistics. The TDC study surveys a representative sample of overnight visitors to the Florida Keys quarterly, excluding cruise ship and day visitors, and applies statistical weighting to project findings to the overall visitor population.

According to the study, approximately 46-47% of overnight visitors to the Florida Keys stay in Key West, equating to about 2.07 million visitors annually. Transportation mode data indicate that roughly 66% of these Key West visitors arrive by car, including both personal and rental vehicles, resulting in an estimated 1.37 million visitors driving onto the island each year.

Additional tourism data, including passenger counts at Key West International Airport, ferry terminals, and cruise ports, support these figures and provide context for visitor arrival patterns. For more detailed information, see the Monroe County Tourist Development Council Visitor Profile Study (2024) here and Key West tourism statistics available through the Key West Chamber of Commerce and Monroe County TDC websites.

Should Key West Be Building Another Downtown Parking Garage?

Posted on January 17, 2026 6 Comments

With this project likely on the way, here’s how we can move beyond the elusive ‘Doris Day parking’ dream to a solution that works for everyone.

Key West officials are looking to build a parking garage on the current City parking lot at Fire Station #2 at Simonton and Angela Streets. The new garage would have a total of 149 parking spaces, a net gain of 85 over the 64 there now. A workshop is being held at 2pm on Tuesday, January 27 at City Hall to discuss the project. (Note: this presentation from the City was added on Jan 23 and here’s our follow up on the Stock Island garage idea.)

Most of us have dreamed of “Doris Day parking”—that perfect, effortless spot right in front of our destination, just like in the movies. But in Key West’s historic district, that dream rarely matches reality. There’s plenty of parking, but it’s seldom that convenient or free and that’s why some people think we need more.

Our initial reaction is we don’t really need more parking on this little island, at least not in our beautiful and compact historic downtown, and that building more parking just induces people to drive more. That, and it’s incredibly tone deaf to be proposing to construct a parking garage while the City and County are dismantling public transit. There’s plenty of parking in and around downtown; we just need to manage the existing supply better and double down on robust transit, safer bike facilities, and better pedestrian infrastructure and amenities.

But the site already is a parking lot and was at one point a parking garage next to the old City Hall. While we’d prefer a garage at Searstown, Stock Island, or Palm Avenue—locations that could intercept cars before they congest downtown and from where we’d shuttle them into the core—this is the garage currently on the table. From what we gather, this project is viewed favorably by City management and most on the Commission dais. So, perhaps IF the resulting new revenue is used to support transit and IF those additional 85 garage spaces could be traded for some number of on-street parking spaces in the nearby neighborhood that could be turned into wider sidewalks and/or bike infrastructure, and they do a few other things, maybe this can be a win-win.

We’re conflicted and asking questions. We all should be. So, in the story below, let’s walk through this together, so that we’re prepared to query City staff and our Commission leaders at that workshop. We’ll look at what parking is out there, the pros for a parking garage, the cons to a parking garage, and some conditions that, if added to the garage project, may make it better. Because in the end, if this project is built, it can’t just be about mainland-style car convenience that clashes with the island’s unique scale, environmental goals, and livability. It has to make our downtown function better for everyone, not just people with cars. Otherwise we should oppose it.

There’s Plenty of Parking Downtown – Just Not “Doris Day Parking”

“Doris Day parking” (urbandictionary.com) is a fun and common term referring to the phenomenon in movies where a character always finds a perfect, convenient parking spot, effortlessly, right in front of their destination. In stark contrast to real life. And while it’s likely only a few of our readers know who Doris Day is, everyone still wants this kind of parking. And that’s the rub. There’s plenty of parking most of the time in downtown – it’s just not right in front of your destination and it’s often not free. So, for many people, the perception is “there’s no parking.” But that’s not the case.

*Doris Day always found parking right out front of wherever she was going* – something that happens a lot in movies.

In a story we did on parking a few years back we heard there may be as many as 10,000+ parking spaces downtown below White Street. Most of these are off-street. There are a few thousand private parking spaces in lodging and retail lots and private driveways. On top of that there’s another 2,000 to 3,000 publicly available for pay parking spaces in private and public lots and garages. Then there are another 3,000+ on-street parking spaces in the downtown core.

Of the 3,000+ on-street spaces, about one-third are metered, one-third are marked Resident Permit Only, and another one-third are unmarked and free for 72 hours – although we believe that in the years since that story some of those unmarked spaces have become metered or Resident Permit. But these are all rough numbers. We understand there may be another 1,000+ on-street spaces uncounted because they are on Old Town blocks (mostly in the South of Truman and Casa Marina neighborhoods) that don’t have curb and gutter and thus aren’t counted in official totals. So, that’s more than 4,000 on-street spaces total. And that’s how you total up to well more than 10,000 spaces.

Of those for pay lots, the City has 11 off-street public lots and garages scattered throughout downtown with about 1,100 total parking spaces. Seven hundred forty-six of those spaces are available to Resident Permit holders for up to 4-hours free of charge. Four hundred six of those spaces are available to employees, who can live outside of the City, and pay for a $30 a month Employee Lot Permit.

In a world where there are already 10,000+ spaces, does 85 new spaces really make a difference?

*This is from the staff consultant’s report.. Here’s a link to it.*

Key Points from City Staff Correspondence

The City believes that adding 85 new parking spaces will make a meaningful difference. Let’s start by examining their perspective.

The City Manager tasked the Engineering and Parking departments with evaluating a multi-level parking garage concept designed to increase parking capacity while minimizing the footprint on the Fire Station 2 site. Previous concepts with fewer levels overwhelmed the site, so this time the consultant was asked to design a garage with a “reduced” footprint. According to the consultant’s report, the main reasons cited for the “Need for Parking Garage” are:

Small shops need more parking for customers and employees.
The proposed garage would add approximately 85 additional parking spaces.
The location is central with easy access from major roads like Eaton Street and Truman Avenue.
Employees must pay regular price to park near their place of employment.
The garage aims to reduce congestion caused by vehicles searching for parking.
Electric vehicle charging stations are planned to support sustainability goals.
Revenue from parking fees would support transit, affordable housing, and other city funds.
Some parking spaces could be reserved for employee permits ($30 a month – not market rate) to alleviate parking pressure in surrounding neighborhoods.

Taking the Staff Points to Task

While some points have merit, as Car-Free Key West, wed be remiss if we didn’t critically examine some of these claims:

Why is it the City’s responsibility, and not the employers’, to provide parking for downtown workers?

Workforce parking seems a major driver for the new garage. Many workers live up the Keys due to a lack of affordable housing on the island, we get that. These employees can’t use the Resident Permit—available only to City residents—and often must seek one of the roughly 1,000+ free spaces in neighborhoods around the commercial core, then walk several blocks. Plenty of public and private garages exist, but workers often don’t want to or can’t afford to pay market rates.

To address this, the City created a $30/month Employee Lot Permit, available to anyone who lives in Monroe County – not just the City, valid at any of the 406 spaces at the Park N Ride garage on Grinnell at the Seaport or the Truman Waterfront Park. With the Duval Loop no longer operating to shuttle workers from these lots downtown, the City now suggests the new garage spaces could be more convenient for some of those who use Employee Permits. However, at $30/month, this reduces revenue from those paying $6/hour, which undermines their revenue argument.

So, why aren’t Key West employers providing free or discounted parking to their employees near their workplaces? Or a Lower Keys Shuttle monthly bus pass? Especially when Federal tax law (Internal Revenue Code Section 132(f)) makes such benefits tax-free for both employers and employees. Tens of thousands of companies across the U.S. offer this routinely. Why not in Key West? Why is the City bailing out employers instead?

*At left is one of those unmarked, free for 72 hours on-street parking spaces. That’s what visitors are searching for and why they won’t park in a garage if they think they can snag one.*

The garage won’t “reduce congestion caused by vehicles searching for parking” unless free parking nearby is eliminated AND better wayfinding signage is implemented.

*Elaine wants George to park in a garage and this is how George responds.*

We’ve written extensively about this issue over the years (here, here, here, and here). The problem boils down to roughly 1,000 to 2,000 on-street, unmarked, free-for-up-to-72-hour spaces. As long as these exist, drivers will be drawn to them like moths to a flame. Or, like George Costanza, they’ll refuse to park in a lot or garage if there’s a chance to find one of those elusive free spaces. While we have no local data, research nationwide shows that up to one-third of a downtowns’ traffic congestion can be caused by drivers searching for parking. So, no, congestion won’t be reduced without addressing the root cause—searching for FREE parking.

*The High Cost of Free Parking by Donald Shoup.*

But don’t take our word for it. Vox has a nice video that explains it: The High Cost of Free Parking and here’s another great video with Adam Conover in Why Free Parking Is Ruining Your City. Or read the book The Hight Cost of Free Parking by Donald Shoup who argues that free or underpriced parking is a major cause of traffic congestion – among other urban maladies.

Additionally, some drivers simply don’t know where to find long-term parking. We need better wayfinding signage before drivers reach downtown (here and here).

Key Points Against the Garage

We won’t focus on aesthetics, architecture, or construction impacts—others can debate those. The site is currently a parking lot and not particularly attractive. Instead, let’s concentrate on the main drawbacks of building this garage:

Adding more parking supply induces more driving (here, here, and here). This is undesirable for any downtown.
The island is small and compact. In the U.S., 52% of all car trips are under 3 miles in length, and 28% are less than one mile. In Key West, these numbers are likely higher, strengthening the case for alternatives to driving (here and here).
Building more parking risks reinforcing mainland-style car convenience that clashes with Key West’s unique scale and sustainability goals. This isn’t Del Boca Vista on the mainland, where travelers on Florida’s US 41 or US 1 expect cars to dominate.
The recent suspension of the Duval Loop transit service highlights a contradictory focus on car convenience over sustainable transportation.
Free on-street parking in Old Town remains abundant and undermines garages and lots (those 1,000+ to 2,000 unmarked spaces mentioned above).
Advocates ask: where is the comprehensive multimodal strategy that integrates this garage and other parking lots with robust transit, improved bike infrastructure, and a more pedestrian-friendly downtown? What’s the plan?

In some of our crowded and vibrant commercial blocks near the proposed garage, like the 500 block of Fleming here, why not take out a few parking spaces for some parakets (left), since we’re adding 85 new spaces nearby. Click to enlarge.

If a Garage Is Built, Here’s What We Need In Addition

If City management and Commissioners proceed with building this garage, let’s help them make it work for everyone—drivers, cyclists, pedestrians, visitors, workers, and residents. Here’s what we suggest:

Dedicate the additional revenue to Key West Transit, not the General Fund.
“Trade” some of the new 85 garage spaces for on-street spaces converted to bike parking, bike lanes, wider sidewalks, or parklets on nearby streets.
- For example, remove parking directly in front of restaurants on parts of the 400 and 500 blocks of Southard Street, part of the 500 block of Fleming Street, and part of the 400 block of Eaton Street to widen sidewalks or install parklets for better café seating that doesn’t interfere with walking.
- Another example is removing private car storage on the 300 block of Duval and widening the sidewalk on the western side, so pedestrians don’t have to walk single file.
Commit to restarting the Duval Loop AND fulfilling the promise in the adopted 10-year transit plan to increase frequency and span of service on existing routes and create new fixed-route service on the island.
Eliminate most or all free on-street parking in the surrounding neighborhood, if not all of downtown. This encourages garage use, supports revenue, and helps reduce congestion (here, here, here, and here).
Work with local bicycle shops to create a bikeshare program based out of the 11 City parking lots to provide easier first-and last-mile connections for parkers. Maybe some of those workers can use the Employee Work Permit at the Park N Ride or Truman Waterfront and bike share to their job?
Improve wayfinding and marketing so people use the garage instead of congesting streets hunting for parking (here and here).
Commit to a comprehensive multimodal transportation plan for downtown.

As we approach the public workshop on the 27th, let’s remember that this project can achieve better results if these items are included. Without them, the project simply doesn’t make sense and should be opposed.

If we want to move beyond the fantasy of ‘Doris Day parking’ and the frustration of circling endlessly, this garage project must be part of a bigger, smarter plan. One that balances convenience with sustainability, supports transit and active transportation, and respects the unique character of Key West. Only then can we turn the elusive perfect parking spot into a practical reality for everyone.

# # #

Don’t Let the TDC Stonewall Using Tourist Monies for Tourist-Serving Transit

Posted on January 11, 2026 1 Comment

Why the City Must Push Monroe County and the TDC to Act Now on Using Tourist Tax Dollars for Tourist-Serving Transit While Also Planning for the Future

At Tuesday’s January 6 Commission meeting, hope was in the air that a little funding for our beleaguered public transit system could be found. It came in the form of a discussion item brought forth by Commissioner Monica Haskell that asked the question: “Should the City seek tourist tax funds to support tourist-serving transit like the Duval Loop?”

Nearly all of the Commissioners said some form of yes, let’s pursue it. The City Manager said he was already on the case too. And a letter of apparent support arrived just before the meeting from Kara Franker, the President and CEO of the County’s Tourist Development Council (TDC). Everything seemed to be aligning nicely for a helpful solution to a funding problem that has bedeviled both the City and County transit programs.

Except upon reading the fine print of Ms. Franker’s letter, which wasn’t available until after the meeting, perhaps it wasn’t as supportive as some thought and cheered. Her phrase “I’m not opposed, in principle” gave us immediate pause. And it seems like she’s sowing the seeds for kicking the can down the road by offering that the “appropriate next step is a deliberate, countywide evaluation of tourist-oriented transportation needs” and that it’s “a topic worth studying thoughtfully.” One can imagine that by the time this is thoughtfully studied and deliberately planned to death over the next few years, the Duval Loop will be a distant memory and more frequent transit on other routes will be too.

No. Absolutely not. We can walk and chew gum at the same time. Yes, Ms. Franker’s correct, we should indeed be planning for the future. But the next budget year that begins October 1, 2026, for which there will be discussions this summer, should include fully funding a free Duval Loop out of Tourist Tax Dollars. And they should add some funding for the Lower Keys “Tourist” Shuttle too. The TDC marketing juggernaut can spare a few million next fiscal year, while they, the County and the City plan for the big stuff. Let’s break it down in our story below.

Recap: Why Tourist Tax Funds for Transit?

Key West’s transit system has faced severe challenges in recent years. The Duval Loop has been suspended, and other transit services have struggled due to unreliable federal and state funding. The County’s Conch Connect and transit department were eliminated for similar reasons, leaving a gap in reliable transportation for workers, residents and visitors.

As we explored in last week’s story, Funding Transit Without Raising Local Taxes: A Win for Tourists and Residents,Tourist Development Tax (TDT) funds, collected from visitors, offer a stable, local source to support transit primarily serving tourists. This approach enhances the visitor experience, reduces congestion, and supports the hospitality industry—all without raising local taxes or burdening residents.

City of Key West leaders on the dias on January 6: Commissioners Greg Veliz, Monica Haskell, Lissette Carey, Mayor Danise “DeeDee” Henriquez, Commissioners Donald “Donnie” Lee, Aaron Castillo and Sam Kaufman.

What Happened at the January 6 Meeting?

The City Commission discussed the idea but did not make any immediate decisions. Key points included:

Haskell and Kaufman Lead: Commissioner Haskell emphasized she wasn’t asking for a reallocation of existing funds but looking at future budgets, reminding everyone that tourists pay these taxes, not residents. Commissioner Sam Kaufman expressed strong support and stressed the need for clear documentation of tourist benefit and coordination with the County.
Calls for Support and Caution: Commissioner Aaron Castillo supported exploring reserve funds and TDC funds as options. Commissioner Veliz said, “Anything we can look at to get more money into transit—I’m for that.” Commissioner Lee urged caution, noting the concept has a long way to go and there are competing interests for TDC money.
TDC’s Position: Kara Franker, President & CEO of the Tourist Development Council (TDC), sent a letter that morning emphasizing that while she is not opposed in principle, any use of TDT funds must comply with Florida law, be fiscally responsible, and equitable across Monroe County. She called for a countywide, long-term transportation strategy rather than piecemeal action.
Budget and Funding Discussions: The Commission discussed potential funding sources, including reallocating funds from reserves or future budgets, but no commitments were made.
Mayor Directs Next Steps: The Mayor directed the City Manager to work with the County and report back, signaling ongoing collaboration.

This discussion reflects cautious optimism but also highlights the need for clear plans and cooperation across jurisdictions to move forward effectively.

*At left, TDC CEO Kara Franker and at right Monroe County Commissioner Holly Merrill Raschein, Mayor Michelle Lincoln, Commissioner Jim Scholl, Mayor Pro Tem David Rice, and Commissioner Craig Cates.*

Our Take: The Ball Is in Their Court, But It Should Move Faster

The “Their” in this subtitle primarily refers to Monroe County and the Tourist Development Council (TDC), who control the allocation of Tourist Development Tax funds. However, the City of Key West also has a critical role to play. The City must actively insist and collaborate with the County and TDC to ensure timely and decisive action on funding tourist-serving transit. While the responsibility is shared, the urgency demands faster movement from all parties involved.

Kara Franker’s call for a thoughtful, countywide strategy is reasonable and necessary, but it risks delaying much-needed improvements. The transit crisis is immediate, and the Duval Loop is already designed to serve tourists. There is no need to reinvent the wheel or wait years for a comprehensive plan before allocating some funds. Here are two key actions that should happen now:

1. Fund the Loop and Enhance the LKS in the 2027 TDC Budget

We believe the County and TDC could easily allocate a few million dollars from next year’s TDC budget to restart and expand a free Duval Loop by October 1, 2026, and enhance the Lower Keys “Tourist” Shuttle, which naturally serves tourist lodging and destinations along US Route 1 between Marathon and downtown Key West. The Loop needs less than $1.5M annually to run a “free and frequent” circulator. And with another $1.5M added to the Lower Keys “Tourist” Shuttle, one could increase the moribund 90-120 minute current frequencies down to 60 minutes or less. That’s less than 10% of the current TDC marketing program.

This approach would:

Provide immediate relief to visitors and reduce congestion.
Demonstrate commitment to sustainable tourism and transit.
Leave other funding sources available to support resident-serving transit.

And for goodness sake if there’s any leftover money from some source of unused funds, start sooner than October 1.

2. Plan for Transit and Its Funding for the Future

This video shows Monroe County’s vision for the future of transit in the Florida Keys – before they dismantled their transit department over the summer. The point is they already had plans.

The City of Key West has an adopted 10-Year Plan that is just a little more than one year old. While not as formalized, the County had a long-term transit plan that included 30-minute trunk service along the Overseas Highway from Key Largo to downtown Key West, supplemented by a series of circulator and on-demand services in the villages up and down the Keys. Start with these, figure out how much money they need and what portions can be realistically funded by TDT funds as “tourist-serving” transit. And then figure out how we come up with the balance of funds needed.

The City and County Should Take Action NOW While Planning for the Future

*The City adopted a good 10-year plan in December of 2024.*

Tourist Development Tax funds are allocated at the County level, so the City of Key West must actively engage Monroe County and the Tourist Development Council (TDC) to take decisive action. These funds represent a vital resource that can be reinvested in visitor-serving transit to boost the tourism economy and improve quality of life for all.

To avoid being caught flat-footed during the summer’s budget session, the County and TDC need to begin their due diligence immediately. This means lining up all necessary legal, fiscal, and procedural steps to allocate approximately $3 million for tourist-serving transit without delay.

At the same time, the City and County must initiate a long-term transit planning process that includes securing more stable funding. While reorganizing existing revenues in the next fiscal year is part of the solution, there may also be opportunities to increase the Tourist Development Tax within the limits allowed by state law. Exploring these options now will ensure a sustainable transit future for the Florida Keys.

Delaying action risks losing momentum and prolonging transit challenges that hurt workers, residents, and businesses alike. Your voice matters—urge local leaders to prioritize immediate funding for visitor-serving transit and to plan strategically for the years ahead.

Together, we can build a more accessible, less congested, and visitor-friendly Keys for everyone. Waiting too long risks procedural delays that could push funding decisions well beyond the next fiscal year.

# # #

Contact your Monroe County Commissioners, TDC Board Members, and contact Key West Mayor and Commissioners

Chris Hamilton is the founder of Friends of Car-Free Key West & Duval Street/Historic Downtown, a local advocacy group championing sustainable mobility and vibrant public spaces. Subscribe to the blog and follow on Facebook, Twitter, and Substack for updates. All stories are cross posted at KONK Life News. Originally from Washington, D.C., Chris spent over two decades leading nationally acclaimed initiatives in transit, biking, walking, and smart growth for Arlington County, VA’s DOT. Since moving to Key West in 2015, he has embraced a car-free lifestyle downtown, dedicating his time to non-profits and community projects. Explore all Streets for People column articles here.

Funding Transit Without Raising Local Taxes: A Win for Tourists and Residents

Posted on January 4, 2026 2 Comments

How Commissioner Haskell’s January 6 Discussion Could Change the Game

By now, most know that 2025 was a challenging year for public transit in the Keys and Key West. Monroe County dismantled its fledgling transit department and Conch Connect service, while the City of Key West suspended its popular downtown circulator, the Duval Loop. Both governments blamed cuts to Federal and State transit funds, but the responsibility lies with them to plan better and not rely on these volatile sources.

The impact? Workers and residents are left stranded without reliable transit options, and tourists—77% of whom arrive by car—are forced back onto those vehicles to get around, causing congestion and parking problems. But as we enter 2026, hope rises with the upcoming City Commission meeting on January 6, offering a chance to begin addressing this crisis.

Commissioner Monica Haskell, who has persistently championed this issue since early summer has placed a Discussion Item (#34) before the City Commission. She asks, “Do we support seeking tourist tax funds to fund tourist-serving transit like the Duval Loop?” The accompanying information she provides states this will “enhance the visitor experience, alleviate congestion, and bolster the hospitality industry.”

These are compelling reasons for all Commissioners to support and vote yes.

In the story below, we explore why tourist funds are essential, how this approach could work and the legal basis for using this source of monies. We also examine how it benefits not only tourists but also workers, residents, and the hospitality industry we all rely on. We hear from business leader Paul Menta and Commissioner Sam Kaufman and explain how you can urge the Mayor and Commissioners to back this crucial initiative for our island’s future.

Why Tourist Tax Funds?

Category	Amount	Source
Monroe County TDT Revenue (FY 2024)	$61.5 million	FY 2024 Annual Report (PDF)
Transit Funding from TDT	$0	FY 2024 Annual Report (PDF)
Marketing Spend	Estimated $30–40 million	FY 2024 Annual Report (PDF)

Most of the funding for Key West Transit has come from Federal and State transit sources and grants, with the remainder from parking fees, fares, and advertising revenue. No General Fund or local tax dollars have ever been used. While staff have begun exploring other smaller innovative funding sources, these efforts will make only tiny dents in the funding gap. Relying on unstable State and Federal transit dollars has created a boom-and-bust cycle, preventing the realization of ambitious 10-Year plans. This underscores the need for a reliable, stable local funding source like tourist taxes.

Tourist Development Tax (TDT) funds come from taxes paid by visitors, not residents. Using these funds to support transit services primarily serving tourists does not increase general taxes or burden local taxpayers. Instead, it leverages the money tourists already contribute to enhance their experience and reduce congestion. This is why we also advocate exploring cruise ship disembarkation fees and more dedicated parking fees—costs largely borne by tourists.

What the Law Allows Regarding TDT Funds

In our August 31 story, Could Tourist Dollars Be the Answer to Our Transit Funding Problem?, we explored the specific legal framework governing the Tourist Development Tax (TDT) and what it permits. Florida Statute §125.0104(5)(a)(6) clearly allows TDT funds to be used for transportation systems designed to increase tourist-related business activity. This includes capital projects and services that primarily serve tourists.

Transit services such as the Duval Loop and Lower Keys Shuttle, which connect hotels, attractions, and beaches, fit squarely within this statute—especially when ridership data demonstrates their role in serving visitors. Commissioner Haskell’s information item also affirms this interpretation.

Further backing this, a Florida Attorney General Opinion AG 217-06 confirms that transportation services must be designed and promoted as part of the tourism experience to qualify for TDT funding.

This legal clarity strengthens the case for using tourist tax funds to support transit services that enhance the visitor experience while benefiting the local economy.

Some have questioned whether Tourist Development Tax funds can legally support transit like the Duval Loop and Lower Keys Shuttle. The key is that these services are designed primarily for tourists. The Duval Loop is explicitly designed to serve visitors, connecting hotels, attractions, and key destinations. In fact, City surveys have said that upwards of 80% of riders are tourists. The Lower Keys Shuttle, by running along US Route 1—the only road in the Keys—naturally serves all hotels and tourist spots. While the route itself may not change, branding and marketing can emphasize its role as a tourist-serving transit system.

Florida’s Attorney General Opinion AG 217-06 confirms that if a transit service primarily serves tourists and is promoted as part of the tourism experience, it qualifies for TDT funding. This aligns with Commissioner Haskell’s information item and the legal framework outlined in Florida Statute §125.0104(5)(a)(6).

This approach ensures that tourist tax dollars are reinvested to enhance the visitor experience, reduce congestion, and support the hospitality industry—benefiting both tourists and the local economy.

Future Use of TDT Funds?

Our August 31 story suggested that perhaps some of the $60M-plus TDT revenue collected in 2024 could be redirected. Specifically, we highlighted a portion of the $30-$40 million currently spent on marketing as a potential source. Commissioner Haskell’s information item notes that Florida Statute §125.0104 allows counties to add an additional 1% to 2% tourist tax, which would require a local referendum and approval by the county commission.

It’s not yet clear whether Commissioner Haskell is proposing to reallocate a portion of existing funds or to pursue an increase in the tax to support transit. This will likely be a key point of discussion at the January 6 meeting. Regardless, her direction signals a positive step toward securing sustainable funding for visitor-serving transit.

Benefits of Tourist-Serving Transit

Transit is a strategic investment in tourism that amplifies the island chain’s appeal and markets the free-and-easy spirit that makes the Keys unique.

Enhances Visitor Experience: Reliable transit connecting key tourist destinations makes exploring the city and islands easier and more enjoyable.
Alleviates Congestion: Reducing car traffic in popular areas helps preserve the charm and accessibility of Key West and neighborhoods throughout the Keys.
Supports the Hospitality Industry: Easier movement for visitors means more business for hotels, restaurants, and attractions, and helps residents reliably get to work without the expense of owning a car.

In addition, transit can reinforce TDC messaging and branding by using participating vehicles as rolling billboards and placing TDC information on the outside and inside of buses and at stops. Real solutions paired with smart marketing amplify the island’s appeal.

The TDC advertises Key West and the Florida Keys as something different. And it is. But if visitors have to deal with the same car-centric, traffic congestion and parking problems they have on the mainland, it ruins the experience.

Business Leader Paul Menta and Commissioner Kaufman Support Use of TDT Funds for Tourist Serving Transit

“I urge both the City and County to move quickly to make it happen.”

Sam Kaufman has long been a vocal proponent of public transit and bicycles. This past summer was no exception as he led the charge to try and save the Duval Loop. In the end it wasn’t enough, but he held City management to the task by saying he excepted them to come back in a few months with plans for new funding from TDT, cruise ship, parking and other sources to not only save the Duval Loop but to implement the long term plans that call for more and better service on all the routes. Here’s what he said when we asked him about Item #34 on the January 6 docket:

“Transportation services like the Duval Loop and the Lower Keys Shuttle are essential infrastructure for Key West. They reduce congestion, support our workforce, enhance the visitor experience, and help residents and tourists move safely and efficiently through our city. I strongly support using Tourist Development Council funding for these services, and the City should do everything it can, and as quickly as possible, to restore the Duval Loop now that service has been suspended. These transit investments also support climate resilience by reducing vehicle miles traveled, promote reduced traffic congestion in our historic downtown, and make it more realistic for working families to live and work here without relying on multiple vehicles. This is exactly the kind of smart, forward-thinking public policy that benefits residents, visitors, and our local economy, and I urge both the City and County to move quickly to make it happen.”

“Tourism Dollars Need to Support Tourism Transportation.”

We’ve been quoting Paul Menta, leader of the Shop Mom and Pop Key West business group and owner of the Key West First Legal Rum distillery for years as a proponent for better public transit, safer bike routes and affordable housing. Here’s what he had to say when we asked him about Commissioner Haskell’s initiative:

“As we step in the 2026 and we see what is hoping to be a busier tourist season, it brings a smile to my face to see more bicycles than ever all over town as people get around. The Duval Loop, which is a nice perk for tourists, cannot take money from our public transportation for the elderly and our workers. Tourism dollars need to support tourism transportation. The city could not afford to do this, and I think with the new transportation coordinator creating new routes for workers making it easier for them to get to their workplaces is just as important as workforce housing. Also, our senior citizens need places to sit and shade, and you have to have a budget for this. I believe that the Loop and the rest of the City’s transit routes should be separate entities. I travel a lot in this world and generally transportation is not free for tourism. Got to put the oxygen mask on ourselves first, keep riding those bikes!”

Paul has a point. By spending tourism dollars on tourist serving transit, it should free up money to improve the City’s other transit services. Paul has been advocating for more frequent and better spans of service, and he says the City should make this as much a priority as workforce housing. Amen!

Let’s Support Commissioner Haskell’s Initiative

Depending upon federal and state grants to fund public transit has proven foolhardy over the years. Using TDT funds is just one of a number of potential new local non-property tax or general fund sources that should be looked into. But for today, using TDT funds for tourist-serving transit and thus supporting this initiative on January 6 is a win-win, no brainer.

While the initiative requires approval by the County Commission and possibly a local referendum, it is important to emphasize that this funding approach does not divert general tax revenues. It is a strategic reinvestment of tourist dollars into infrastructure that benefits tourism and the local economy.

The City Commission should endorse seeking tourist tax funds to stabilize and expand visitor-serving transit. This is an investment in Key West’s future as a premier tourist destination and a more accessible, less congested city.

Commissioner Haskell’s question is direct: “Do we support using tourist tax funds for transit like the Duval Loop?”

The answer is a clear and resounding YES.

# # #

Contact Your Key West Mayor and Commissioners:

Key West Commissioner Directory
Mayor Danise “DeeDee” Henriquez: mayor@cityofkeywest-fl.gov
Monica Haskell (District 1): DistrictI@cityofkeywest-fl.gov
Samuel Kaufman (District II): DistrictII@cityofkeywest-fl.gov
Donald “Donnie” Lee (District III): DistrictIII@cityofkeywest-fl.gov
Lissette Carey (District IV): DistrictIV@cityofkeywest-fl.gov
Greg Veliz (District V): DistrictV@cityofkeywest-fl.gov
Aaron Castillo (District VI): DistrictVI@cityofkeywest-fl.gov

Submit an eComment: Visit the City legislative website here, look for the date of the meeting and at the far right you’ll see a button for eComment. Here’s a direct link to Item 34.

Chris Hamilton is the founder of Friends of Car-Free Key West & Duval Street/Historic Downtown, a local advocacy group championing sustainable mobility and vibrant public spaces. Subscribe to the blog and follow on Facebook, Twitter, and Substack for updates. All stories are cross posted at KONK Life News. Originally from Washington, D.C., Chris spent over two decades leading nationally acclaimed initiatives in transit, biking, walking, and smart growth for Arlington County, VA’s DOT. Since moving to Key West in 2015, he has embraced a car-free lifestyle downtown, dedicating his time to non-profits and community projects. Explore all Streets for People column articles here.

Bikes Gain Ground, Transit Faces Crisis: Key West’s 2025 Transportation Story

Posted on December 21, 2025 Leave a Comment

As 2025 draws to a close, it’s clear that this year has been a defining one for transportation and urban mobility in the Keys and Key West. Our 24 stories this year reveal a tale of two contrasting trends: meaningful progress in bicycle infrastructure and advocacy, alongside significant setbacks in public transit.

The year saw our community make strides toward safer, more accessible cycling options including new bike lanes, kickoff of a new Safety Action Plan and a brand new bike bridge, among other projects, that promise a more bike-friendly future. Meanwhile, transit services faced severe challenges, with the County ending its transit program entirely and the City suspending its flagship Duval Loop service. These changes have left many workers, residents, and visitors grappling with fewer reliable options to get around without the expense of owning a car.

In our story below we’ll briefly review the island’s advances on the bicycle front and examine what’s gone wrong with transit. We’ll also touch on how the resignation of the Planning Director fits into the larger theme of transit’s collapse. As well as look at how the erasing of our rainbow crosswalks sparked local engagement and hope amid these shifts.

*A brand new Staples Avenue Bike Bridge, a bike-friendly roudabout on the Crosstown Greenway, new bike lanes on South and United Streets and a not so secret path lead to happy bicyclists.*

Progress on Bicycle Infrastructure

The year began with a spark of controversy when Commissioner Donnie Lee raised concerns about e-bike safety, igniting a community-wide conversation that ultimately left more questions than answers (Commissioner Lee Is Right. It’s Time To Get Fast Moving E-Bikes Off of Our Promenades, January 10)). Today, the most promising path on a solution on e-bikes lies with the Safety Action Plan committee (Zero Fatalities by 2035 – Key West Aims for Safer Street for All, July 27), which is actively identifying projects and policies aimed at making the island safer for cyclists, pedestrians and drivers. This plan represents a significant step, and we eagerly anticipate its completion in 2026.

Infrastructure improvements marked the year, with the completion of new bike lanes on South and United Streets downtown (Rebuild of South Street Is Complete and Includes New Bike Lane, January 27) standing out as a major milestone. The opening of the upgraded Staples Avenue Bike and Pedestrian Bridge (The Crosstown Green – The Locals Not So Secret Bikeway, November 7) further enhanced connectivity, alongside a bunch of ongoing efforts, including roundabouts, signage, data collection and upcoming initiatives at many of the intersections along the almost 4 mile long Crosstown Greenway route.

Looking ahead, the question posed in our story Could Key West Become the Paris of Small Cities? July 1 captures the optimism of the moment. With our compact size, favorable weather, and walkable urban grid, Key West has the potential to become a model city for biking with continued commitment and effort.

Transit in Crisis

*The City’s newly adopted 10-Year Transit Plan and the County’s Conch Connect started the year with promise.*

Early Promise and Optimism

The year began with hope as the County’s Conch Connect micro-transit service showed promising signs of success, earning praise for its innovative approach to local transit (Just Six Months Old, Conch Connect Micro-Transit Is Already Beating Expectations, January 24). This service offered a glimpse of what a responsive, flexible and well-branded transit system could look like for the Keys. And just months before that at the end of 2024 the City adopted an ambitious 10-year Transit Development Plan that promised expanded service and new routes.

Beyond Conch Connect, the County had ambitious plans to expand transit service across the island chain. The vision included a 30-minute trunk line running the length of the Keys, providing frequent, reliable service along the main corridor. This would be complemented by neighborhood circulators and on-demand transit options designed to serve local areas and provide first-and last-mile connections. These plans represented a forward-thinking approach to transit, aiming to create a network that was both comprehensive and adaptable to community needs. Unfortunately, these promising plans were never fully realized, as the County’s transit program was abruptly dismantled early in the summer (Conch Disconnect: County Scraps Transit Service for Local Workers, July 20 and Conch Disconnect: Repeal Without Replace Is Just Regression, July 24) and the City’s plans came undone slowly over the the same time period.

The Summer Collapse

In what proved to be a foreboding of bad things to come, in June, the City announced that the Duval Loop would begin charging $1 per trip starting in July—a move we covered and criticized as penny wise and pound foolish (The $1 Mistake: How Key West Is Undermining the Duval Loop, Again, July 6 and Making the Duval Loop Free and Easy Helps Downtown Prosper, July 14).

It wasn’t until the end of July, during budget season, that the potential permanent cuts became clear. Both the County and City seemed to unravel as preliminary budgets were released, and Federal and State grants—funding sources they arguably should not have been relying on—began to dry up. The County abruptly ended Conch Connect and disbanded its entire transit department, while the City suspended the Duval Loop service amid financial pressures, while congratulating itself for not cutting other services. Neither entity appeared to have planned ahead or taken public transit seriously enough to ensure continuity. The result has been a severe reduction in transit options, leaving many workers, residents, and visitors with fewer reliable ways to get around without a car (Dumb and Dumber Transit Cuts: A Failure of Leadership In the Keys, August 3 and Transit Is Collapsing In the Keys. Will Business Leaders Let It? August 17).

*Workers up and down the Keys left stranded with no transit alternatives.*

Community Impact and Response

Our coverage throughout the summer and fall documented the fallout from these decisions that wouldn’t officially be codified until budgets were adopted in September. With no more Conch Connect, trip requests initially surged on the similar Key West Rides overwhelming the service, and community frustration grew palpable. Many stories highlighted how these cuts disproportionately affected workers and residents who depend on affordable, reliable transit daily. Business leaders (especially Paul Menta) and city officials (most notably Commissioners Sam Kaufman and Monica Haskell) have stepped into the conversation, exploring alternative solutions and advocating for restored and improved transit options (Even If You Never Ride the Bus, You’ll Feel It When It’s Gone, August 24 and Key West Rides Overwhelmed After Conch Connect Shutdown – City Pushes Alternative Buses Amid 36% Spike In Trip Requests, August 26).

Leadership and Funding Challenges

The transit crisis has exposed significant leadership voids and funding shortfalls. The County’s decision to end its transit department and the City’s budget-driven suspension of the Duval Loop reflect a lack of coordinated planning and investment. These challenges raise urgent questions about the future of transit in Monroe County and the City, underscoring the need for renewed commitment and innovative funding strategies (Duval Loop Eliminated: A Tragedy and a Turning Point, September 14 and No Director. No Department. No Direction: Monroe County’s Transit Collapse, September 21).

A vivid example of these leadership challenges came in September with the resignation of Katie Halloran, the City’s Director of Human Resources (Katie Halloran’s Quiet Revolution, September 7). In a public letter, Halloran detailed a hostile work environment, understaffing, and a lack of responsiveness to internal complaints. Her departure highlighted deeper organizational dysfunction within City government, which has compounded the difficulties in managing transit and other essential services. This story adds a human and institutional dimension to the transit crisis, illustrating how internal struggles at City Hall have further undermined efforts to maintain and improve public transportation in 2025.

Looking to the future, our article Could Tourist Dollars Be The Answer to Our Transit Funding Problem? August 31 offers a critical lens on potential solutions. As 2026 approaches, the community’s focus must turn to securing sustainable funding and leadership to rebuild and reimagine transit services that truly meet the needs of all who live, work, and visit the Keys.

Rainbow Crosswalks: A Symbol of Community and Hope

Among the challenges of 2025 we’d include the erasing of our rainbow crosswalks at Duval and Petronia by the State of Florida. But something remarkable happened as the community banded together first in protest and then for solutions that included installation of rainbow bike racks and a future rainbow welcome arch. These vibrant symbols celebrate diversity and foster local engagement and hope during a year marked by transit setbacks and infrastructure debates. Our stories (From Rainbow Crosswalks to Rainbow Museums, September 10 and This Is Just the Beginning Rainbows Return to Duval, October 7) highlight how such initiatives contribute to the city’s cultural fabric and community spirit, inspiring ongoing conversations about inclusion and public space.

*The threat of erasing the Rainbow crosswalks galvanized the community. The rainbow bike racks bring back hope.*

Looking Ahead to 2026

As we move into 2026, the challenges facing transit demand renewed focus and innovative solutions, that we hope are captured in our recent article After the Loop’s Gone, What’s Next for Key West Transit, November 29. Meanwhile, the momentum behind cycling and safer streets offers hope for a more balanced, sustainable transportation future in the Keys.

Thank you for following along this year. We look forward to continuing this vital conversation and advocacy in the year ahead because an island that is bike, walk and transit friendly and remembers that our downtown streets are for people first, is a more prosperous, healthy, green, equitable and happy little island paradise.

# # #

Our Most Popular Stories Ranked By Views On WordPress (Doesn’t include KONK Life or Substack Views).

After the Loop’s Gone, What’s Next for Key West Transit?

Posted on November 29, 2025 1 Comment

Even with enhancements underway, reliable funding is key to making transit dependable for workers, residents, and visitors.

About six weeks after our October 12 story asked, “Can Key West Transit Rise Again?” where we detailed the impending cuts and analyzed existing services and plans, transit staff recently laid out a clearer, if still uncertain, path forward at a November 13 public meeting in Bahama Village.

The Duval Loop, a vital circulator route for visitors, workers and residents alike will be officially suspended on December 31, 2025. While the Loop continues to run for a few more weeks, this, we hope, temporary shutdown underscores the ongoing challenges facing City amid budget cuts and shifting funding landscapes.

We learned at the meeting that within the framework of this year’s budget, the Key West Transit (KWT) team is actively making numerous small but meaningful improvements across the system. These include upgrades to bike racks on the buses, backend software enhancements for the Key West Rides on-demand service, farebox modernization, and route fine-tuning on the Lower Keys Shuttle and Workforce Express. At the same time, staff are focused on securing funding to bring the Loop back and improve service frequencies and capacities on other routes. We learned the meeting is part of a broader dialogue KWT wants to have with the community, reflected in public meetings held in November—and with another meeting planned for December, though the date has yet to be announced.

In our story below we’ll go through what we’ve been hearing about these improvements, listen to what the public has to say, discuss why finding reliable funding is consequential to improved service and how we need to stay on top of officials to ensure this all happens.

What We Know So Far: Key Takeaways

Duval Loop

The suspension of the Duval Loop is now official, with the last day of service set for December 31, 2025. However, city staff emphasize that this is a temporary suspension rather than a permanent elimination. There is no set date for when the Loop will restart, but hopes are pinned on the next fiscal year, which begins October 1, 2026. To guide improvements, the city has engaged a consultant to review the Loop’s operations and recommend changes that better integrate potential future mobility hubs.

Working on Improvements This Year That Include:

At the November meeting, Transit Director Rogelio Hernandez shared some exciting updates on the many improvements underway across Key West Transit. These projects tackle rider concerns and operational challenges head-on, aiming to enhance the overall transit experience in tangible ways. Here’s a closer look at what’s happening:

Bike Racks: Key West Transit is installing new bike racks on all buses, increasing capacity from two to three bikes. These upgraded racks are designed to accommodate larger, heavier bikes, including longer and thicker models, directly addressing frequent rider complaints. A cool new feature will provide real-time information on bike rack availability, helping riders know in advance if there is space for their bike. This enhancement encourages multimodal trips by making it easier for cyclists to combine biking with bus travel, a crucial step in expanding transit accessibility and convenience.
On-Demand Software Upgrades: The Key West Rides on-demand service is undergoing backend software upgrades aimed at improving operational efficiency. A key focus is enforcing a no-show policy more effectively to reduce service disruptions caused by riders who book rides (taking up allocated seat space) but fail to show up. Additionally, workers will soon be able to pre-book rides up to a week in advance and specify arrival times, allowing the system to optimize pick-up schedules and improve reliability. By minimizing no-shows and enabling advance booking, the system can better allocate resources and ensure more reliable service for all users, especially workers.
Farebox Modernization is underway, with plans to enable tap payments using credit cards and mobile wallets like Apple Pay. Expected to be operational by spring, this upgrade will streamline fare collection, reduce boarding times, and enhance convenience for riders who prefer cashless payment options.
Route Fine-Tuning efforts include specific adjustments to the Lower Keys Shuttle to address delays caused by driver breaks and refueling stops. These changes aim to shorten trip durations and improve schedule reliability, directly responding to rider feedback about lengthy wait times and inefficiencies.
Electric Bus: Key West Transit is preparing to introduce its first electric bus in January. While it won’t enter service until summer to allow for driver training, this vehicle represents a significant step toward a cleaner, more sustainable fleet.
Marketing: Outreach efforts will be expanded through a partnership with South Florida Commuter Services, focusing on rebranding, marketing, and community engagement. This collaboration is designed to boost public awareness and ridership by improving communication channels and conducting targeted outreach to better connect with the community. These are the same folks who originally branded the Duval Loop and Car-Free Key West and we’re glad to see them back to help out.
New Planning Software: The adoption of new transit planning software will support future service changes and public outreach initiatives. This advanced tool will enable data-driven decision-making and facilitate more effective engagement with the public as Key West Transit evolves its services. A key part is inputting data from Key West Rides to better pinpoint needs of the fixed route services.

Community Reaction

Since we began covering potential cuts to both County and City transit services on July 1, the community’s response has been vocal and heartfelt, reflecting the deep reliance many have on public transit for daily mobility. The Duval Loop, in particular, has become a symbol of effective transit that helped keep tourists out of their cars, eased parking and congestion, and connected people to shops, restaurants, and key destinations. This importance is underscored by the fact that five of our top 10 stories over the last six years were focused on transit cuts just this summer, with our social media pages also full of public angst.

At the November public meetings, workforce transit reliability and accessibility remained top concerns. Many emphasized that dependable service is critical for employees who rely on buses to get to work on time. Business leaders like Paul Menta, of Shop Mom and Pop Key West, highlighted the tangible impact of transit cuts on their employees, stressing that reduced service threatens workforce stability and local economic vitality. Menta noted that many of his employees depend on transit, and cuts could worsen staffing challenges already felt across the local economy.

*Transit Director Rogelio Hernandez chats with customer Pati Crimmins at the Nov. 12 meeting at the Douglas Gym.*

Riders shared mixed feedback about the Duval Loop. While all appreciated its role in connecting key destinations, some pointed to frustrations with its route length and frequency. The announced suspension has raised worries about accessibility and convenience, especially for those who depended on the Loop for daily errands and commutes. Transit staff acknowledged these concerns and emphasized their commitment to bringing the Loop back in an improved form, alongside ongoing efforts to enhance amenities and service reliability across the system.

Additional feedback from the first public meeting in November included suggestions to explore late-night or 24-hour service options to better accommodate residents and workers with non-traditional schedules. Concerns were raised about the “Seat Unavailable” prompt on the Key West Rides app, which some found unclear or frustrating when booking rides. There were also worries about the ability of some riders, especially seniors, to use the on-demand Key West Rides app effectively. One rider expressed a preference for multiple small, fixed-route loops around the island instead of the current Uber-like on-demand buses.

Transit Director Rogelio Hernandez said outreach efforts would focus on seniors and underserved communities, aiming to ensure that transit remains equitable and responsive to all residents’ needs. Community feedback continues to shape planning and service adjustments.

One longtime resident reflected on the Duval Loop as “the best idea I’ve seen the City of Key West come up with,” expressing hope that with Rogelio Hernandez at the helm, funding will be found to rejuvenate this essential route. Paul Menta noted that workers use the Duval Loop to navigate downtown after being dropped off by the Lower Keys Shuttle and expressed concern that they might give up on transit once the Loop is gone. However, he told officials that if new funding is secured, the priority should be better service for workers, including increased frequency on the Lower Keys Shuttle and Workforce Express, noting how many downtown workers now live further up the Keys.

Feedback gathered over the summer also underscored the community’s reliance on transit and the importance of maintaining and improving service despite budget challenges. These voices continue to inform the ongoing dialogue between transit staff and the public.

Together, these perspectives paint a picture of a community deeply invested in the future of Key West Transit, eager for solutions that balance fiscal realities with the need for reliable, accessible transportation.

Funding: The Crux of the Matter

It was encouraging to hear about all the new projects and improvements staff are working on, but for transit to truly improve — with more services, higher frequencies, and longer, reliable hours that serve workers, residents, and visitors — the system needs more funding. As local business leader Paul Menta emphasized, the City must take transit as seriously as it does affordable housing, because transit is just as critical to the community’s well-being and economic vitality. We agree wholeheartedly with Paul!

Key West’s transit system has long relied heavily on grants, and they must have mentioned going after more grants half a dozen times at the meeting. While we applaud wanting not to tax locals, grants should be used to enhance service, not fund its base. It is the overreliance on this kind of funding that has contributed to the boom and bust cycle of cuts and uncertainty and never fulfilling the long-term plans. In fact, this year it led to the suspension of the island’s best-used service.

To break this pattern, city and county leaders need to get creative and explore new local revenue sources that can stabilize and expand transit services sustainably. Discussions are ongoing with County officials, and there is interest in tapping into cruise ship and Tourist Development Council (TDC) funds as potential revenue streams.

Monica Haskell, who attended the November meeting, mentioned she is still actively working with the Tourist Development Council, highlighting ongoing collaboration efforts to explore funding opportunities.

Many of the revenue-generating ideas and cost-saving strategies discussed by the internal staff Transportation Coordination Team (TCT) — including increased parking violation fines, improved Park N Ride signage, special event surge pricing, advertising opportunities, and the new tap-to-pay fare system — have been incorporated into this year’s budget or are actively being pursued. Transit staff is also exploring operational efficiencies through improved routing, vehicle types, fuel alternatives, and other strategies to reduce expenditures

While these efforts are promising and nibble around the edges, a reliable, steady local funding source is still needed as the base to truly improve and expand transit. Cruise ship and TDC funds could and should be part of that solution.

Over the summer, our coverage has highlighted the funding challenges and the urgent need for innovative solutions. Without a stable and dedicated funding source, restoring and enhancing transit services — including bringing back the Duval Loop and improving frequencies on key routes — will remain difficult.

Our leaders at the City and County face a critical moment to prioritize transit funding and ensure the system can meet the community’s needs now and into the future.

For more on the potential of tourist dollars to solve transit funding challenges, see our related story: Could Tourist Dollars Be the Answer to Our Transit Funding Problem?

What to Watch For and Looking Ahead

As we continue to follow Key West Transit’s evolving story, there are several key developments to watch closely. Ongoing public engagement will shape the future of transit services, with community feedback playing a critical role in guiding decisions. The new partnership with South Florida Commuter Services promises to enhance outreach, marketing, and rider engagement, helping to build stronger connections between transit and the community.

Funding strategies and partnerships remain central to the system’s sustainability, with updates expected as city and county leaders explore creative revenue sources. Progress on mobility innovations, including planning tools and service improvements, will also be important indicators of how transit adapts to changing needs.

Continued collaboration between the City and County will be essential to securing a stable future for Key West Transit.

Looking ahead, our coverage will remain committed to providing timely updates from meetings, developments, and community conversations, ensuring that residents, workers, and visitors stay informed about the transit system that serves them.

This ongoing dialogue underscores why transit matters so deeply to Key West — it is a lifeline for many, a key to economic vitality, and a cornerstone of the city’s vision for a sustainable, accessible future.

# # #

Recent transit stories leading up to today’s:

After the Cuts Can Key West Transit Rise Again? October 12, 2025
No Director, No Department, No Direction: Monroe County’s Transit Collapse September 21, 2025
Duval Loop Eliminated: A Tragedy — and a Turning Point September 14, 2025
Could Tourist Dollars Be The Answer to Our Transit Funding Problem? August 31, 2025
Even If You’ll Never Ride the Bus, You’ll Feel It When It’s Gone August 24, 2025
Transit Is Collapsing in the Keys. Will Business Leaders Let It? August 17, 2025
Dumb and Dumber Transit Cuts: A Failure of Leadership in the Keys August 3, 2025

Chris Hamilton is the founder of Friends of Car-Free Key West & Duval Street/Historic Downtown, a local advocacy group championing sustainable mobility and vibrant public spaces. Subscribe to the blog and follow on Facebook, Twitter, and Substack for updates. All stories are cross posted at KONK Life News. Originally from Washington, D.C., Chris spent over two decades leading nationally acclaimed initiatives in transit, biking, walking, and smart growth for Arlington County, VA’s DOT. Since moving to Key West in 2015, he has embraced a car-free lifestyle downtown, dedicating his time to non-profits and community projects. Explore all Streets for People column articles here.

Why Key West Ruins Everything — And Why I’m Still Grateful to Call It Home

Posted on November 27, 2025 Leave a Comment

Every Thanksgiving, I find myself reflecting on how grateful I am for wonderful family and friends, but above all, how fortunate we are to call this place home.

This story originally took shape two Thanksgivings ago. I was musing that we’d left wonderful lives in the District to take a chance on Key West, and my love for this place has deepened since. So, this is an ode to how genuinely wonderful our little island paradise is, and how lucky and grateful I am to call it home.

Today, our car-free lives here are enriched by engaging in vibrant traditions and events that happen year-round or just enjoying the peace and tranquility of our always lush balcony. We’re blessed to work with the most wonderful, creative and wacky people at two venerable and always fun Duval Street mainstays: Mikey at La Te Da, where he’s been going strong for nearly 9 years, and me at the Red Barn Theatre, where I’m approaching 7 years.

Where else in the USA can one spend an afternoon or two a week, 12 months a year, at clothing optional pool bars? For us these jaunts remain a cherished ritual — a time to hang out with the local gang, unwind, connect, and soak in the island’s free-spirited vibe. For me, Sundays culminate in the glorious outdoors Tea Dance at La Te Da, a long-held 40+ year tradition hosted by DJ Rude Girl, where the music and dancing – I’m often the first and last person on the dance floor – carry on the island’s enduring culture and One Human Family community.

We’ve also just hosted our 4th Annual Fantasy Fest People’s Parade Balcony Party, a highlight of the year where friends bring and hand out thousands of beads and shots, as we party with neighbors, other locals and visitors together in celebration and joy. But this is just part of the tale of our love for Key West.

Join me below in reliving the story I shared on November 23, 2023, as we revisit the journey and celebrate what I believe is Key West’s greatest asset — its people.

Originally published on November 23, 2023:

Key West Ruins Everything Or Why I’m Grateful to Call Key West Home

December 1 marks Mikey and my 9^th anniversary of arriving to live in Key West. And for that decision we are very thankful this holiday. We left a good life in the District. Jobs we loved, family and friends developed over decades, season tickets to the Nationals and Redskins, a cute condo in a hip and thriving neighborhood near the trendy U Street Corridor, favorite café’s, an unparalleled ethnic food scene that we readily took advantage of, and a cool bikeshare and pervasive transit system that made it easy and inexpensive to hop about town without a car. Life was good. But here we are getting ready to celebrate our 9^th holiday season on the island. Key West has that kind of effect on people. It draws visitors in and makes them dream of, well, as the book says quitting your job and moving to Key West.

Which we did. And never for a moment have we regretted making the decision to uproot all we had going in D.C. and take a chance on life where we didn’t know a soul and had no work. Boy, do we love it here and consider ourselves fortunate to be residents and workers on this island.

Everyone who calls Key West home, and I’m including snowbirds, part-timers, and regular visitors because we love and need them all, have their own reasons to be thankful, but for us it starts with the fact that we’re urban rats and prefer a city-life where you can bike and walk to all of life’s needs. (Walkscore 94 and Bike Score 100) And living in Key West makes that easy. Being able to live car-free keeps life simple and more connected to our glorious surroundings. Oh, and it certainly helps us better afford the high cost of living in a sought after vacation destination.

*Those who get this reference are my kind of people. Wink.*

We are grateful to live smack dab in the middle of North America’s largest historic district of wooden structures. Old Town is simply beautiful and reminds us of our old neighborhoods in D.C. and Old Town Alexandria – although those were brick. And our balcony overlooking Fleming Street provides us with ideal 12-months-a-year outdoor living while allowing us “front porch” viewing of a vibrant city life below.

Wearing shorts and t-shirts and being able to swim 12 months a year is an amazing plus. And saves money on wardrobe. It keeps us healthy too as we’re more apt to get out and about for exercise. And for my friends and family up north, yes, we have changing seasons, they’re just a lot more subtle.

It’s an easy, breezy, simple, and relaxed life because well, we’re all on Key West time. And everywhere we turn there’s the ocean, the gulf, or the seaport. Oh, and unlike in D.C., where we were often the oldest people wherever we went, now we seem to be the median age. It’s nice to live in a place that accepts us as we are. Which leads me to the main reason we are so gratified to live here. THE PEOPLE!

Maybe it’s because we’re such a small town so you get to know everyone. Wherever you go there’s a hello or a hug. Or maybe it’s because Key West attracts the best of humanity. We’re an island of misfits, and people on their second and third lives. We’re known to attract artists and creative types. And dreamers. And dropouts. And people who love to party and cut loose. And people who like to quietly paint, write or curl up with a good book. There’s always something to do and there’s always the option just to waste away.

We live and let live and are willing to give anyone the benefit of the doubt. We’re generous to a fault – witness there’s a fundraiser every single week of the year, and resilient in the face of obstacles. We’re just too small a town not to include everyone and that spirit is embodied in our One Human Family slogan. It’s uplifting and hopeful and fun to live in a place with this kind of spirit and love. As a result, we’re blessed with amazing co-workers and lovely friends. I’ve never witnessed and felt this kind of close-knit and connected community.

So, you can have your mainland and your mainland ways of life. As Mikey said to me a few years ago, “Key West ruins everything!” And it does. Because living anywhere else just pales in comparison and so ruins it for us. I’m just so very thankful and grateful to live here.

# # #

Chris Hamilton is the founder of Friends of Car-Free Key West & Duval Street/Historic Downtown, a local advocacy group championing sustainable mobility and vibrant public spaces. Subscribe to the blog and follow on Facebook, Twitter, and Substack for updates. All stories are cross posted at KONK Life News. Originally from Washington, D.C., Chris spent over two decades leading nationally acclaimed initiatives in transit, biking, walking, and smart growth for Arlington County, VA’s DOT. Since moving to Key West in 2015, he has embraced a car-free lifestyle downtown, dedicating his time to non-profits and community projects. Explore all Streets for People column articles here.

The Crosstown Greenway — The Locals’ Not-So-Secret Bikeway

Posted on November 7, 2025 1 Comment

Key West’s Crosstown Greenway is a quiet triumph — a safe, slower bike route that threads through the quiet heart of the island, offering locals a way to avoid the chaos of N. Roosevelt Boulevard, the heavy traffic on Flagler and the long loop around the promenade on S. Roosevelt. Starting at Duck Avenue and S. Roosevelt, the Greenway weaves through a couple of improvised cut-throughs before winding along Staples Avenue, Von Phister, Reynolds, and finally connecting to South and United Streets downtown. It’s not just a path — it’s a story of community persistence, smart planning, and ongoing investment.

Recent data from a permanent counting dashboard installed on the Staples Avenue Bridge shows that roughly 1,100 people cross the bridge daily, with about 900 cyclists and 200 pedestrians. Since the bridge sits at the midpoint of the Greenway, this number offers a strong proxy for the volume of people traversing the route each day.

In our story below we examine how the path was born, some of the recent improvements including a roundabout, a new bike/ped bridge and new bike lanes to connect to the heart of downtown and plans for future improvements. With the City in the middle of developing a Safety Action Plan, the Crosstown Greenway takes on greater importance as the safe route of choice to cross east to west across the island. Let’s take a look more closely…

*The Crosstown Greenway is indicated by the blue lines through the middle of the island.*

🚲 How the Greenway Was Born

The Crosstown Greenway didn’t start with a master plan — it started with locals who saw a better way. Tom “The Bike Man” Theisen and then–Bike Coordinator Jim Malcom were early champions, piecing together a safe route through the middle of the island in the very late 1990s to early 2000s.

One of their first victories was securing a right-of-way across Housing Authority property between 12th Street and Kennedy Street. At the time, the Housing Authority had fenced off access, forcing bikes to either use a dumpster ramp on the tall Housing Authority building or detour a couple of blocks to Flagler Avenue and “salmon” — that is, ride against the flow of traffic on a narrow sidewalk. This affected everyone — workers, tourists, and kids heading to school.

After Hurricane Georges, Tom launched a guerrilla campaign. He cut plywood into square signs, stenciled “Henry’s Blockade” (a jab at Housing Authority director Henry Haskins), and screwed them to the fence. The signs were removed as fast as he put them up. He also organized a letter-writing blitz to the Citizen, enlisting friends to sign each one to bypass the paper’s submission limits. Eventually, Jim Malcom stopped by Tom’s house with good news: the Housing Authority would grant the right-of-way.

*Top photos show the cut through from Kennedy at left and 12th at right across Housing Authority right-of-way. Solid green line on map show the same.*

Funding stalled the project until Jim found leftover concrete from another job. Just like that, the path went in — a mix of old sidewalk and fresh concrete. It’s still in use today.

Another key link was the path through the Wickers Sports Complex parking lots — a quiet connector that helped form the original “Locals’ Bikeway.” Combined with the Staples Avenue Bridge, these segments gave residents a car-free alternative to Flagler Avenue and N. Roosevelt Boulevard.

Jim Malcom, who passed away in 2008, was instrumental in these early efforts. Known for his tenacity and commitment to accessibility, he pushed for ADA-compliant ramps and curb cuts across the city, often ruffling feathers but making lasting change.

The City formally embraced the route in March 2019, when it was designated the “Crosstown Connector” in the Key West Bicycle and Pedestrian Master Plan. The idea was and is, to use low density neighborhood streets with low volumes of traffic (Seidenberg, Staples, Von Phister) and further enhance their safety with traffic calming measures as an alternative to heavier trafficked, but sometimes more direct streets (N. Roosevelt or Flagler). The slow, leafy residential nature of the route is why it is today referred to as a Greenway.

*In 2021 volunteers helped City staff show how small, targeted improvements could enhance the Crosstown Greenway.*

From Recommendations to Real Change

As improvements began — from green paint to new bike lanes — the name quietly shifted to the “Crosstown Greenway,” reflecting its growing role as a safe, people-first corridor. What started as a locals’ workaround is now a centerpiece of Key West’s mobility future.

This is where the City began to seriously pick up on the recommendations from the Bicycle and Pedestrian Master Plan and start turning ideas into action. Volunteers and advocates showed how small, targeted improvements — like green paint and quick-build projects — could make streets safer and more welcoming for people on bikes and on foot.

This momentum led to tangible improvements: wayfinding signage on poles and painted directly on the street, the Staples Avenue Bridge replacement, the installation of the new mini roundabout, and the permanent bike counter on the bridge. These projects mark a turning point, demonstrating the City’s commitment to safer, more accessible streets and the ongoing evolution of the Crosstown Greenway.

🚧 A Bridge Worth Celebrating

The Staples Avenue Bike/Ped Bridge is more than just a crossing — it’s a cornerstone of the Crosstown Greenway. Originally installed about 25 years ago after contentious community meetings pitting neighbors afraid of gas-powered scooters against bicycle advocates wanting a simple, straightforward path. A trans quadriplegic in a motorized wheelchair regularly attended meetings and was a powerful advocate for inclusive, straightforward design.

As Tom Theisen recalls, “The biking community (also) wanted a straight approach but was tired of fighting the neighbors at that point.” So, eventually the bridge was shaped by compromise: bikers had to get off the street and use the sidewalks to access the bridge. Bollards were added down the middle of the bridge to calm traffic. The sidewalks and bollards, meant to scare away the scooters, also made it very difficult for bike riders, many of whom had to dismount to traverse the bridge as a result, especially for tricycles. But it was still way better than the alternative routes and so was heavily used.

We’re told the original bridge was championed by passionate commissioners, including Merili McCoy and Jeremy Anthony, who faced fierce opposition from neighbors. With the rise of e-bikes, some of those concerns have resurfaced, and Tom concedes the neighborhood is now “tormented” by them.

*The 25 year old bridge, dismantled in 2024, was difficult to navigate because of compromises to keep scooters out.*

Plans for a new and better bridge started about five years ago in 2020 when we reported on issues of rusting and corrosion reported by kayakers under the bridge. The City Engineering Department immediately responded and said although the bridge was safe, it was nearing the end of its useful life and made plans to replace it. After a couple years of funding delays the City announced in 2023 that a new bridge would be built. Work started in 2024 and was completed earlier this year.

Bikes now approach the new bridge straight on from the middle of the street. At 15 feet wide, the replacement structure is much wider, allowing for two-way bicycle traffic and a separated pedestrian walkway. No more navigating onto the sidewalk and curving around onto the bridge. No more pesky bollards in the middle to crash into. No more bike vs. pedestrian incidents. Easier to cross. Safer for everyone. A huge improvement.

Despite its importance, the bridge never got a grand opening ceremony when it was rebuilt and finished earlier this year. But its impact is undeniable. It connects key segments of the Greenway and offers a safe, car-free route through the center of the island.

*Crossings from the newly installed counter on the new Staples Avenue Bike/Ped Bridge.*

The Importance of Data: Counting on the Bridge

A permanent counting dashboard was installed on the Staples Avenue Bridge a few months ago, providing valuable data on usage patterns. This data is crucial for informed planning and ensuring the Greenway continues to meet the needs of its users and neighbors.

The dashboard shows that roughly 1,100 people cross the bridge daily, with about 900 cyclists and 200 pedestrians — a testament to the bridge’s vital role as a key artery for safe, car-free travel across the island.

*The new traffic circle at the intersection of Staples Avenue and 4th Streets.*

The Roundabout That Got People Talking

The paint is still drying on the recent reconstruction of the intersection of 4th Street and Staples Avenue that included replacing the existing two-way stop controls with a neighborhood traffic circle, as recommended in the Key West Bicycle and Pedestrian Master Plan. This change was designed to accommodate larger turning radius vehicles while improving traffic control in all directions to minimize collisions, reduce vehicle emissions, decrease traffic control disregard, and enhance pedestrian crosswalks as part of the Crosstown Connector.

The project had long been in the works, approved by the City Commission and supported by the Sustainability Advisory Board. While some residents were surprised by the new mini roundabout, it reflects the City’s commitment to safer, more efficient streets.

“Modern Mini Roundabouts can certainly be part of the plan… but we should ensure that we don’t create problems for people with low or no vision.” — Ryan Stachurski

Though the final design lacks a landscaped island, it includes pavement markings and raised markers to guide traffic. It’s a modest but meaningful step toward safer streets. And our friend Tom Thiesen says:

”The roundabout at 4th is a great improvement and should be implemented on the whole bike route.”

We agree with Tom that there are plenty of opportunities for more of these along the route. Especially as he points out there’s about three dozen stops along the entire route. Either that or perhaps implement the Idaho Stop, that allows for cyclists to treat stop signs as yield signs, for bikes along the Greenway.

*To navigate the jury-rigged path through Wickers Field, bicyclists must navigate two, often flood prone parking lots.*

The Proposed Wickers Path: Progress and Challenges

The Wickers Path is a key segment of the Crosstown Greenway, winding through the area once home to the Wickers Stadium, a minor league baseball park from 1969 to 1975 — we wrote about the history here: In Quest to Improve Crosstown Greenway, City Prepares to Construct New Bike Trail Segment. Today, the site is known as the Wickers Sports Complex, bounded by 14th Street, Kennedy Drive, Flagler Avenue, and Poinciana Elementary School.

This short but crucial trail segment connects the concrete cut-through path from Seidenberg Avenue between 12th and Kennedy through two parking lots serving the sports complex before reaching Duck Avenue at 14th Street. Currently, this area is an unsafe mess, with bikes and cars sharing tight spaces.

In May of 2021, we reported that Commissioner Sam Kaufman and then-Commissioner Greg Davila championed efforts to separate bike traffic from the parking lots to improve safety for all users. At the time, Multi-Modal Coordinator Ryan Stachurski told us that Calvin, Giordano and Associates completed their report on the project, and design alternatives were expected shortly, with construction initially slated for summer 2021.

However, the project has faced delays and challenges, including drainage issues that proved the allocated funding inadequate to overcome those problems. Initial funding remains allocated, but construction was pushed back from 2027 to 2029, with a likely need for value engineering due to budget constraints. Additionally, the presence of the new Flagler pump station and fire station on the Wickers property requires redesign efforts.

This project has seen fits and starts, but the commitment to improving this critical connection remains strong among advocates and city officials alike as Wickers Path remains a vital piece of the Crosstown Greenway.

*New, where none existed before, bike lanes downtown on South and United connect to the Greenway.*

Downtown Extension: South & United Streets

The City of Key West has recently completed major rebuild projects on United Street and South Street, bringing brand new, wider bike lanes and improved pedestrian safety to these critical downtown corridors.

The United Street rebuild, finished in 2024, included a $4.8 million investment in new curb and gutter, narrower and safer pedestrian crossings, fresh asphalt, abundant new trees, and a wider bike lane where none had existed before. This new bike lane heads out of downtown and connects seamlessly with the Crosstown Greenway and other bike facilities, helping create a safer, more connected network.

Following closely, the South Street rebuild wrapped up in early 2025 with a $3.5 million investment. It features new paving, ADA-compliant sidewalks and curb ramps, improved drainage, landscaping, and a new inbound bike lane designed to be 4 feet wide with a 2-foot buffer, totaling 6 feet. While slightly narrower than state minimum standards for door-zone bike lanes, it is wider than many existing lanes in Key West and represents a significant safety upgrade.

Together, these two projects act like a bike lane pair similar to the Fleming and Southard Streets lanes, providing safer, easier routes for cyclists traveling into and out of downtown. They also connect to the Reynolds Street bike lanes, which lead to Higgs Beach and beyond, enhancing the overall bike network on the island.

Then Mayor Teri Johnston had been a vocal supporter of these improvements, as has Commissioner Sam Kaufman, emphasizing the importance of dedicated bike lanes to keep bikes and e-bikes off sidewalks and improve traffic flow while maintaining parking.

Ryan Stachurski, Multi-Modal Transportation Coordinator, highlighted the complete streets elements incorporated in these projects, including bicycle wayfinding signs, street trees for shade, and design features reinforcing the 20 MPH speed limit to promote safety and support the City’s Vision Zero goal.

These new bike lanes and pedestrian improvements mark a major step forward in Key West’s commitment to safer, more accessible streets for all users.

*More wayfinding signage is coming as well as a study on the crossing at Duck Ave. and S. Roosevelt.*

What’s Next for the Greenway

The Crosstown Greenway is a sprawling, evolving project with many moving parts. According to Ryan Stachurski’s April report, several key initiatives are on the horizon:

Completing wayfinding confirmation signage across the entire route to help users navigate more easily.
Installing complete street features, some embedded or funded within the Von Phister Street resurfacing project, though not all details have been finalized.
Continuing progress on the roundabout at 4th Street and Staples Avenue and the Wickers Path, both covered earlier in this page.

Where Duck Avenue Meets S. Roosevelt

Additionally, the City is actively pursuing grant funding to study improvements at the Duck Avenue and S. Roosevelt intersection, a critical entry point to the Greenway. Advocates have long called for enhanced safety measures here, including a traffic light or pushbutton flashing beacons, as detailed in our previous coverage here: “Do We Need a Traffic Light at Duck Avenue and S. Roosevelt?“. The Sustainability Advisory Board supports this grant effort, and the City is open to community input. While construction may be years away, securing early design funding could accelerate the timeline.

We’ll point out that Tom Thiesen suggests that Eagle Avenue is a safer alternative than busier and more congested Duck Avenue. We agree and often use Eagle ourselves when getting to S. Roosevelt from the Greenway. But the problem of safely crossing the four lanes of traffic on S. Roosevelt would still need to be overcome. So we applaud studying options.

Other Intersections That Need Safety Features

From a safety perspective, there are other busy crossings along the Greenway that need attention, including White Street, First Street, 5th Street and Kennedy Street. In addition to the crossing why oh why does Kennedy Street need four lanes of vehicle traffic?

Both the Bike/Pedestrian Master Plan and Ryan’s recent updates highlight White Street as a priority for improvements. For example, bulb-outs could shorten crossing distances and enhance pedestrian safety where sidewalk expansion is limited. And green paint could be applied across the street to alert cars to the presence of the Greenway.

Von Phister Targeted Next

The Von Phister Street resurfacing project is backed by $500,000 in grant funding. It primarily involves mill and pave work and shoulder restoration but aims to lock in some of the temporary improvements from the original pilot project, such as sharrows and wayfinding signage. Sidewalk improvements may be limited due to space constraints, but safety enhancements like bulb-outs at White Street are under consideration. The project design is expected to be done mostly in-house, with construction planned for this year. Official project documents are available here.

The Crosstown Greenway: A Path Worth Investing In

The Crosstown Greenway isn’t just a shortcut — it’s a statement. It shows what happens when a city listens to its residents, prioritizes safety, and builds for the future. With continued investment, clearer markings, and community support, this not-so-secret bikeway can become a signature feature of Key West’s mobility landscape.

Encouraging more people to get on bikes not only reduces congestion and emissions but also makes life on our island healthier, safer, and more enjoyable for everyone. The Greenway’s evolution is a testament to what’s possible when community advocacy meets smart planning and sustained commitment.

Ryan Stachurski sums it up well:

“The Crosstown Greenway is an important facility for residents and visitors as not only does it provide a comfortable bicycle route for students to get to school and families to get to the game – but it means fewer cars on the road and less parking congestion at the destination. Workers who take the route don’t displace car-parking spaces that might otherwise be used by customers. Slower-speed roads with safe crossings correlate with fewer injuries that can be catastrophic for vulnerable road users and their families.”

Stay tuned for ridership data and more updates as the story unfolds.

Together, we can keep moving Key West forward — one pedal stroke at a time.

# # #

Chris Hamilton is the founder of Friends of Car-Free Key West & Duval Street/Historic Downtown, a local advocacy group championing sustainable mobility and vibrant public spaces. Subscribe to the blog and follow on Facebook, Twitter, and Substack for updates. All stories are cross posted at KONK Life News. Originally from Washington, D.C., Chris spent over two decades leading nationally acclaimed initiatives in transit, biking, walking, and smart growth for Arlington County, VA’s DOT. Since moving to Key West in 2015, he has embraced a car-free lifestyle downtown, dedicating his time to non-profits and community projects. Explore all Streets for People column articles here.

After the Cuts: Can Key West Transit Rise Again?

Posted on October 12, 2025 1 Comment

Perhaps, if the plan is followed—and funded—there’s still a way forward.

Note on October 14, 2025, two days after we posted the story below, the Key West Transit Director, provided this memo to the City Commissioners via the City Manager that Duval Loop service would be suspended on December 31. He also provided this summary of the Loop changes and some minor changes to the Lower Keys Shuttle as well as a communications and public meeting schedule. Neither the memo nor summary indicates when the Loop may return.

FY2026 Begins with Uncertainty and a Promise

FY2026 begins not just with budget cuts—but with a question: can public transit in the Keys survive this moment, and maybe even emerge stronger? Monroe County’s system has collapsed. Key West Transit is shrinking. And yet, the Duval Loop still runs. Promises are being made. Plans are on the books. The question isn’t just what’s happening—but what could happen next.

The City has cut $1.3 million from its transit budget and is slated to “suspend” the Duval Loop sometime soon. We think. Meanwhile, Monroe County’s Conch Connect was canceled, and its transit department and director eliminated. It’s a moment of reckoning for public transportation in the Keys.

So, we’re taking stock. What services remain? What do the numbers say? And what does the future look like under the City’s 10-Year Transit Plans—adopted last winter and previously in 2019? And we’ll discuss what needs to happen next. Let’s dive in…

Duval Loop: Still Running, Still Uncertain

Although FY2026 began on October 1, the Duval Loop is still running—despite lacking dedicated funding to sustain it all year. That’s a hopeful sign.

Transit Director Rogelio Hernandez told us his team “has a date in mind” for shutting down the service and will “share that information with everyone soon.” He emphasized that the Loop isn’t being eliminated but “suspended,” adding:

“It’s not a goodbye, just a ‘see ya later.’ The Duval Loop will be back, and it’ll be even better.”

He also noted:

“There are some other improvements in the pipeline, and we will be happy to share more information as we get closer to implementation.”

Mr. Hernandez, who’s been director since spring, seems more determined than past leadership to find sustainable local funding to enable him to build the program. Maybe they’ll figure something out and keep the Loop running. We’ll find out when the public does—and we’re hoping for the best.

Ridership Reality Check

Transit systems live or die by their numbers. In Key West, those numbers don’t just reflect how many people ride—they help determine how much funding the system receives from state and federal sources. Ridership is up overall, about 2% vs last year, but only because of one route. Without the Duval Loop, the picture looks worse than it is.

Here’s the updated annual ridership for FY2025 (October 1, 2024, through September 30, 2025):

Duval Loop: Up 15%, from 125,655 to 144,385. But after the $1 fare was introduced, ridership dropped 45% in the final 3 months vs the first 9 months and dropped 8% vs the same three months the year before.
Lower Keys Shuttle: Ridership is 3% down—97,522 vs 100,533 last year.
Key West Rides: Down 15%, with 70,458 rides this year vs 82,699 last year.
Workforce Express: Up 11%—18,399 vs 16,581 last year but still not a lot of rides.

Worth noting: despite initial reports that Key West Rides was overwhelmed after Conch Connect shut down on August 15 (which had 65,000 rides last year), August and September ridership for Key West Rides (5,425 + 5,674) was actually 11 percent lower than the same two months the previous year (6,345 + 6,056). So, the impact has yet to show up in the data. And where did Conch Connect’s rides go?

*Data provided by Key West Transit. Click on image to enlarge.*

Share of total ridership this fiscal year:

Duval Loop: 44%
Lower Keys Shuttle: 29%
Key West Rides: 21%
Workforce Express: 6%

Looking at the bigger picture: Annual total ridership in Key West has fluctuated significantly over the past decade:

Since the pandemic, ridership has increased each year—a positive trend. But 44% of that total now comes from the Duval Loop. In FY2016 and FY2017, before the Loop existed, the system still carried 250,000 to 300,000. And in FY2018 and FY2019 the City Routes were carrying double the current City Routes (KWR + WFE). It begs the question, what was working then?

The Backbone, The Gamble, and The Question Mark

We’ve discussed the Duval Loop a lot this summer (here, here and here). Three services remain. Each plays a different role—and each faces different challenges.

Lower Keys Shuttle (The Backbone)

With 10 trips a day in each direction, every 90–120 minutes from Marathon to downtown Key West, the Lower Keys Shuttle is the backbone of the remaining system. It’s hasn’t changed in a decade, and last year the City completed a $1.4 million mostly grant funded “final mile” upgrade to all 62 stops: new bike racks, fix-it stations, trash and recycling bins, solar flagging, and posted maps and schedules—a rarity on other routes.

Strong ridership and regional importance make it the strongest candidate for future investment. Riders we talked to on Facebook agree: “If the schedules were more frequent… more people would travel.” Another added, “With 90–120 minute waits… it’s hard to rely on it as regular transportation.”

*Key West Rides data, which covers the period since its inception, provided by Key West Transit. Click on graphic to expand.*

Key West Rides (The Gamble)

Launched in November 2022, Key West Rides replaced the fixed North and South routes with an Uber-like on-demand model. The City hoped to stretch limited drivers and funding by expanding coverage and restoring weekend service—without increasing costs.

But the service hasn’t lived up to its promise. Ridership dropped 15% this year, and pre-COVID fixed routes carried twice as many riders. The model offers flexibility—but lacks scale and reliability.

Riders have voiced frustration: “I’ve had to take Uber home because I couldn’t cancel in time,” said one museum worker. Another writes, “Just bring back regularly scheduled bus routes and run them till midnight.” Another customer chimes in, “I try to use KW rides. 2/3 of the time it is slick, and I’m impressed, but the other 1/3 it is unavailable. It seems the algorithm is set for high efficiency for a few users. Having a full sized bus as a personal ride seems wasteful. It is very frustrating to see almost empty buses going past my building while the app says there are no rides available.” And still another, “It’s a joke. KW Rides never has availability.”

At left is the original Workforce Express route that debuted in June 2023. At right on July 1, 2024 they reconfigured it into a meandering mess that could take almost twice as long to get to downtown. Click to enlarge.

Workforce Express (The Question Mark)

Born from Key West Rides data showing a pattern, the Workforce Express launched in June 2023 to serve commuters from Stock Island to downtown. It started strong: 8 trips a day, a direct 30-minute route from Wreckers Cay to Bahama Village.

Then the City mucked it up—cutting trips to 6 and stretching the ride to 45 minutes to serve more locations. Ridership rose 11%, perhaps that’s where some Conch Connect riders went, but the total still remains low.

One rider says: “I was very disappointed by this change. It’s wrong to claim this is an expansion of service when it’s actually 2 fewer buses a day and they are much less frequent. Changes like this should not be allowed without public meetings.” While another says, “Express…Does not mean all the stops all the time.” And, “What about people who work evenings? There is nothing available.”

Local business leader Paul Menta offered a clear critique: “We should be buying smaller buses and running them more frequently.” He added, “Routes need to drop off at more primary points,” and called for real-time tracking and shelter from the elements.

Taken together, Key West Rides and Workforce Express – the City Routes – now serve half the riders the City Routes (the fixed Orange, Red, Blue and Green) routes did in 2019 or 2018. It begs the question: why?

The Vision That Was: The Transit Development Plans

Plans Were Made. Promises Too.

Since 2020, we’ve chronicled Key West Transit’s evolution—from ambitious planning and public hearings to moments of silence and retrenchment. In 2019, the City adopted a bold 10-Year Plan, held hearings, and promised transformation. In 2024, after much community input and analysis, the City adopted another 10-Year Plan—less visionary, but still expansive.

But time and time again, the ball is placed for a kick—and just like with Charlie Brown and Lucy, it’s pulled away. Aaugh!!! Instead of moving forward, we’ve gone backwards. FY2026 cuts feel familiar—not just in their impact, but in their timing. The question now is whether this time, things really will be different. Lucy is holding the ball and Charlie Brown is lined up for the kick. Stay tuned…

From Vision to Revision

2019 TDP: A Map of Ambition

The original 2020-2029 TDP, adopted in 2019, envisioned a full island-wide network of circulators and connectors that built on the success of the new Duval Loop and existing fixed-routes:

Duval Loop, Midtown Loop, New Town Loop, Old Town Loop, Stock Island Circulator
Airport Connector (South), North Connector and KWIK (Stock Island Garage) Connector
Lower Keys Shuttle

The goal was comprehensive coverage, frequent service, and neighborhood-level accessibility. Transit was imagined as a public good—ubiquitous, reliable, and free.

*Current 2025-2034 Plan map on the left and 2020-2029 Plan map*
*on the right. Click to enlarge each map.*

2024 TDP: A More Measured Approach

The new 2025-2034 TDP, adopted in late 2024, still talks expansion, but it’s more cautious:

North and South Connector fixed-routes make a return
Lower Keys Shuttle gets a frequency boost (from 90-120 minutes now to 60 and eventually 30 minutes)
Duval Loop sees extended hours (7am–12am)
Workforce Express gets a major frequency upgrade (to every 15 minutes)

The 2024 plan proposes phased improvements, aiming to balance ridership gains with cost and efficiency. It’s less about blanketing the city and more about optimizing what’s already there.

*Key West Transit service as it existed in 2019. Click to enlarge.*

What Was Working Then?

The 2019 map of existing services shows a more robust fixed-route system—Red, Orange, Blue, and Green routes, plus the Lower Keys Shuttle—serving key corridors and neighborhoods. These routes predated the Loop and formed the backbone of a more traditional transit network. Riders had predictable schedules, broader coverage, and fewer transfers. The system wasn’t perfect by any measure, but it was functional—and it carried over 300,000 riders without the benefit of a free circulator.

What’s on the Ground Now

Duval Loop is still running—it’s no longer free—and is slated for suspension.
Lower Keys Shuttle remains the backbone, with consistent ridership and regional importance.
Key West Rides has replaced fixed routes with on-demand service, a sharp departure from the 2019 vision.
Workforce Express has expanded to serve more places but remains underutilized due to limited trips.

*Service as it exists today – that is unless the Duval Loop is suspended. Click to enlarge.*

The contrast is clear: before COVID, the City Routes—those intended to serve locals getting around the island—carried twice the number of riders they do today. The Duval Loop then doubled those already strong numbers, proving that demand exists when service is reliable and accessible. The 2019 Plan built on that momentum and envisioned even greater expansion. But after years of retrenchment, the 2024 plan, while scaled to reflect fiscal and political constraints, still added frequency and span to existing routes and even added two new fixed-routes. And now, FY2026 begins not with the renewed investment embodied in that plan—but with cuts.

Timeline: Evolution of City Services

Date	Milestone	Notes
Aug 2017	Duval Loop launches	Free circulator begins service; becomes most popular route.
Dec 2019	10-Year TDP adopted	Envisions island-wide network of loops and connectors.
May 2020	North & South lines introduced	Replace pre-COVID Orange, Red, Blue, Green routes.
Nov 2022	Key West Rides launches	On-demand replaces North/South; weekend service restored.
May 2023	Workforce Express begins	Stock Island to Bahama Village commuter route.
Dec 2024	New 10-Year TDP adopted	Adds frequency, span, and two new fixed routes.
Oct 2025	FY2026 cuts begin	Duval Loop suspended; no new investment.

Transit at a Crossroads: Without Funding a Plan Is Just a Placeholder

The FY2025–2034 TDP is technically still in effect. But are we following it—or drifting in yet another new direction? Previously the City quietly abandoned the 2019 plan saying “conditions have changed within the city” and that the 2019 TDP’s “expansion strategy is now outmoded fiscally and by workforce availability.” Translation: they didn’t have the funding. And now the new plan begins with cuts. It’s like déjà vu all over again.

Without new and increasing sources of real, sustained funding, we are just nibbling around the edges and treading water. So, the first order of business should be to commit to finding money. We’ve discussed the legal case for using Tourist Development Tax (TDT) or TDC funding. Commissioners Haskell and Kaufman have led the charge. The new Transit Director is looking at innovative sources. And at the September budgeting meeting, the City Manager and his finance team signaled a willingness to look at big ticket revenue: TDT funds, cruise ship disembarkation fees, expanded parking revenue and more.

So, what’s next for the City?

The Plan picks up on some things that were working pre-covid and that people asked for: more frequency on existing routes and new, simple direct, fixed-routes.

But we haven’t seen a roadmap from the City for the year ahead and implementing the Plan. And Monroe County? No plan at all.

What Needs to Happen Next

To move from retrenchment to renewal, Key West Transit needs more than promises—it needs action. Here’s what must happen:

Keep the Duval Loop running while funding is secured
Implement the 2024 TDP with clear timelines, public updates, and measurable goals
Increase frequency on the Lower Keys Shuttle and Workforce Express
Restore fixed-route service, as called for in the Plan, and when this happens simplify the meandering WFE
Use Key West Rides to fill gaps—not replace the backbone of fixed routes
Secure More Monroe County funding to add frequency on the Lower Keys Shuttle and Workforce Express to reflect the LKS’ regional role and WFE importance to Stock Island as a first step
Monroe County needs to get back in the game as a second step and implement the wonderful plan they laid out for the future
Both the City and County need to pursue new revenue sources—TDT funds, cruise ship fees, parking revenue, tolls, and grants

(County plan here)
These aren’t just technical fixes. They’re steps toward a system that serves workers, residents, and tourists—and builds a better life for everyone who calls the Keys home.

Closing: A Call to Action

We’ve laid out the facts. The ridership. The plans. The cuts. The history. And yes, the failures. But we’ve also seen glimmers—of leadership, of public pushback, of possibility. The Duval Loop isn’t gone. The Plan isn’t dead. And the people working on this—the under appreciated and under-staffed Transportation team, Commissioners, the City Manager—deserve support.

We’re not naïve. We’ve seen Lucy pull the football before. But we’re still here. Still watching. Still hoping. Because if Key West can build a transit system that works—for workers, for residents, for tourists—it won’t just move people. It’ll move us as a community forward.

# # #

Recent transit stories leading up to today’s:

No Director, No Department, No Direction: Monroe County’s Transit Collapse September 21, 2025
Duval Loop Eliminated: A Tragedy — and a Turning Point September 14, 2025
Could Tourist Dollars Be The Answer to Our Transit Funding Problem? August 31, 2025
Even If You’ll Never Ride the Bus, You’ll Feel It When It’s Gone August 24, 2025
Transit Is Collapsing in the Keys. Will Business Leaders Let It? August 17, 2025
Dumb and Dumber Transit Cuts: A Failure of Leadership in the Keys August 3, 2025

Chris Hamilton is the founder of Friends of Car-Free Key West & Duval Street/Historic Downtown, a local advocacy group championing sustainable mobility and vibrant public spaces. Subscribe to the blog and follow on Facebook, Twitter, and Substack for updates. All stories are cross posted at KONK Life News. Originally from Washington, D.C., Chris spent over two decades leading nationally acclaimed initiatives in transit, biking, walking, and smart growth for Arlington County, VA’s DOT. Since moving to Key West in 2015, he has embraced a car-free lifestyle downtown, dedicating his time to non-profits and community projects. Explore all Streets for People column articles here.

1 2 3 … 25 »