Blog Category

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

Before You Build, You Measure: The Data and Planning Gaps Behind a $6M Garage Streets for People  |  Friends of Car-Free Key West & Duval Street/Historic Downtown  |  Chris Hamilton  |  January 31, 2026 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 […]

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

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 Streets for People  |  Friends of Car-Free Key West & Duval Street/Historic Downtown  |  Chris Hamilton  |  January 24, 2026 While Key West officials are meeting on January 27 to discuss plans for a new parking garage at […]

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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. Streets for People  |  Friends of Car-Free Key West & Duval Street/Historic Downtown  |  Chris Hamilton  |  January 17, 2026 Key West officials are looking to build a parking garage on the current City parking […]

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

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 Streets for People  |  Friends of Car-Free Key West & Duval Street/Historic Downtown  |  Chris Hamilton  |  January 11, 2026 At Tuesday’s January 6 Commission meeting, hope was in the air that a little […]

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

How Commissioner Haskell’s January 6 Discussion Could Change the Game Streets for People  |  Friends of Car-Free Key West & Duval Street/Historic Downtown  |  Chris Hamilton  |  January 4, 2026 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 […]

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

Streets for People  |  Friends of Car-Free Key West & Duval Street/Historic Downtown  |  Chris Hamilton  |  December 21, 2025 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 […]

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

Even with enhancements underway, reliable funding is key to making transit dependable for workers, residents, and visitors. Streets for People  |  Friends of Car-Free Key West & Duval Street/Historic Downtown  |  Chris Hamilton  |  November 29, 2025 About six weeks after our October 12 story asked, “Can Key West Transit Rise Again?” where we detailed the impending cuts and analyzed existing […]

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

Streets for People  |  Friends of Car-Free Key West & Duval Street/Historic Downtown  |  Chris Hamilton  |  November 27, 2025 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 […]

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

Streets for People  |  Friends of Car-Free Key West & Duval Street/Historic Downtown  |  Chris Hamilton  |  November 7, 2025 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 […]

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After the Cuts: Can Key West Transit Rise Again?

Perhaps, if the plan is followed—and funded—there’s still a way forward. Streets for People  |  Friends of Car-Free Key West & Duval Street/Historic Downtown  |  Chris Hamilton  |  October 12, 2025 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 […]

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