Qualla: Key West: The End of the Road and the Beginning of Everything

Key West: The End of the Road and the Beginning of Everything: Introduction

Mon, 12 Jan 2026 00:00:00 GMT

Photo credit Stefan Kokemüller, CC BY-SA 3.0. Key West is as far as you can drive in the continental United States and still be in the United States. The island sits 90 miles from Cuba, closer to Havana than to Miami, at the end of the Overseas Highway that crosses 42 bridges to connect the Florida Keys. The isolation created a culture unlike anywhere else in America: tolerant, eccentric, vaguely Caribbean, thoroughly committed to enjoying life. Writers came - Hemingway, Tennessee Williams - drawn by the light and the liberty. Presidents came too, seeking fishing and escape. The island has been pirate haven, wrecking capital, naval base, and tourist destination. The southernmost point, marked by a concrete buoy perpetually surrounded by tourists waiting for photos, represents one ending and many beginnings.

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Image: Stefan Kokemüller | CC BY-SA 3.0

Key West: The End of the Road and the Beginning of Everything: The Island

Mon, 12 Jan 2026 00:00:00 GMT

Photo credit File:Key West 2008 (2338775214).jpg: CedarBendDrive from USA derivative work: Georgfotoart, CC BY 2.0. Key West is a coral and limestone island four miles long and one mile wide, the last inhabited key before the empty Dry Tortugas. The Spanish called it Cayo Hueso (Bone Key) for the indigenous remains found there; English speakers corrupted this to Key West. The location made it ...

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Image: File:Key West 2008 (2338775214).jpg: CedarBendDrive from USA derivative work: Georgfotoart | CC BY 2.0

Key West: The End of the Road and the Beginning of Everything: The Characters

Mon, 12 Jan 2026 00:00:00 GMT

Photo credit Andreas Lamecker, CC BY 2.5. Ernest Hemingway lived here from 1931 to 1939, writing 'For Whom the Bell Tolls' and 'To Have and Have Not' in a studio above his garage. His house is now a museum; descendants of his polydactyl cats still roam the grounds. Tennessee Williams wrote much of 'A Streetcar Named Desi...

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Image: Andreas Lamecker | CC BY 2.5

Key West: The End of the Road and the Beginning of Everything: The Culture

Mon, 12 Jan 2026 00:00:00 GMT

Photo credit User: (WT-shared) Bz3rk at wts wikivoyage, CC BY-SA 3.0. Key West was accepting of gay residents decades before most of America. The 'Conch Republic' - declared in 1982 as a protest against federal roadblocks - expresses the island's separatist streak. The nightly sunset celebration at Mallory Square has evolved into organized tourism ...

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Image: User: (WT-shared) Bz3rk at wts wikivoyage | CC BY-SA 3.0

Key West: The End of the Road and the Beginning of Everything: The Connection

Mon, 12 Jan 2026 00:00:00 GMT

Photo credit Averette (Marc Averette), CC BY 3.0. The Overseas Highway, completed in 1938, finally connected Key West to the mainland. Henry Flagler's railroad had reached the island in 1912, an engineering miracle of bridges across open water, only to be destroyed by the 1935 Labor Day Hurricane. The highway used the railroad's...

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Image: Averette (Marc Averette) | CC BY 3.0

Key West: The End of the Road and the Beginning of Everything: Visiting Key West

Mon, 12 Jan 2026 00:00:00 GMT

Photo credit Ebyabe, CC BY-SA 3.0. Key West is located at the end of U.S. Route 1, approximately 160 miles southwest of Miami via the Overseas Highway. The drive is scenic and slow - allow four hours minimum. Flights serve Key West International Airport from several mainland cities. The island is walkable; bicycle...

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Image: Ebyabe | CC BY-SA 3.0