Qualla: Key West: The End of the Road

Key West: The End of the Road: Introduction

Thu, 15 Jan 2026 00:00:00 GMT

Photo credit Stefan Kokemüller, CC BY-SA 3.0. The Overseas Highway ends at mile marker zero in Key West, the southernmost point in the continental United States, closer to Havana than to Miami. The island has always attracted people running toward something or away from something - pirates, wreckers, cigar makers, writers, dropouts, gay men when nowhere else was safe, and tourists who want to believe they've reached the end of the line. Hemingway wrote 'To Have and Have Not' here, Tennessee Williams finished 'A Streetcar Named Desire' here, Jimmy Buffett invented his Caribbean-adjacent persona here. Key West declared itself the 'Conch Republic' in 1982 as a protest against Border Patrol checkpoints; the secession was a joke, but it captured the island's attitude toward the mainland. Key West is America's weirdest city, and has been since before weird was a brand.

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Image: Stefan Kokemüller | CC BY-SA 3.0

Key West: The End of the Road: Hemingway's Island

Thu, 15 Jan 2026 00:00:00 GMT

Photo credit Acroterion, CC BY-SA 4.0. Ernest Hemingway lived in Key West from 1931 to 1939, writing 'For Whom the Bell Tolls' (mostly), 'To Have and Have Not,' 'Green Hills of Africa,' and short stories including 'The Snows of Kilimanjaro.' The Hemingway Home on Whitehead Street is now a museum, famous less for its l...

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Image: Acroterion | CC BY-SA 4.0

Key West: The End of the Road: The Conch Republic

Thu, 15 Jan 2026 00:00:00 GMT

Photo credit Edgar Serrano, CC BY-SA 3.0. On April 23, 1982, the Florida Keys seceded from the United States. The provocation was a Border Patrol checkpoint on the only road to the mainland, creating traffic jams and implying that Keys residents were foreigners requiring inspection. Mayor Dennis Wardlow declared independ...

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Image: Edgar Serrano | CC BY-SA 3.0

Key West: The End of the Road: Duval Street

Thu, 15 Jan 2026 00:00:00 GMT

Photo credit Cristo Vlahos, CC BY-SA 4.0. Duval Street runs from the Gulf of Mexico to the Atlantic Ocean - about a mile, though it feels longer at night. The 'Duval Crawl' is the traditional bar-to-bar migration, from Captain Tony's (where Hemingway actually drank, before Sloppy Joe's moved) to the Green Parrot to small...

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Image: Cristo Vlahos | CC BY-SA 4.0

Key West: The End of the Road: Literary Island

Thu, 15 Jan 2026 00:00:00 GMT

Photo credit Averette at English Wikipedia, CC BY 3.0. Hemingway wasn't alone. Tennessee Williams lived on Duncan Street and wrote here; his play 'The Rose Tattoo' is set in a Keys-like Gulf community. Robert Frost wintered here. Elizabeth Bishop lived here for years. Judy Blume lives here now. The Key West Literary Seminar has attra...

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Image: Averette at English Wikipedia | CC BY 3.0

Key West: The End of the Road: Mile Marker Zero

Thu, 15 Jan 2026 00:00:00 GMT

Photo credit Radomianin, CC BY-SA 4.0. Key West International Airport (EYW) is tiny, with limited flights; most visitors drive the Overseas Highway from Miami (160 miles, over 40 bridges including the Seven Mile Bridge). The Southernmost Point buoy - continental USA's tip, 90 miles from Cuba - is photographed constant...

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Image: Radomianin | CC BY-SA 4.0