Should Key West Be Building Another Downtown Parking Garage?

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.

January 17, 2026. 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.

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?

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?

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

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.

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?

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.

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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.