Palm-lined Key West Road
Palm-lined Key West Road

Key West: The End of the Road

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5 min read

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.

Hemingway's Island

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 literary associations than for its population of six-toed cats - descendants of a cat Hemingway supposedly received from a ship's captain. The house and its cats draw hundreds of thousands of visitors annually. Hemingway's life here involved deep-sea fishing (his boat Pilar is replicated at the dock), drinking at Sloppy Joe's Bar, and a complicated domestic life with his second wife Pauline. He left for Cuba in 1939; Key West kept his memory.

The Conch Republic

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 independence, symbolically attacked a man in a Navy uniform with a loaf of Cuban bread, surrendered one minute later, and applied for foreign aid. The 'Conch Republic' was satire, but effective - the checkpoint was removed. The incident became civic mythology. Keys residents are 'Conchs' (pronounced 'konks'), the Conch Republic flag flies everywhere, and the annual Conch Republic Independence Celebration in April keeps the joke alive. The attitude it represents - don't mess with us, we're not like the rest of Florida - is genuine.

Duval Street

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 smaller establishments in between. Key West has no open container law; drinks flow onto the street. The sunset celebration at Mallory Square, featuring buskers, food vendors, and the ritual of watching the sun sink into the Gulf, draws crowds every evening. Duval Street is touristy, expensive, and often excessive, but it captures Key West's fundamental character: a party at the end of the road.

Literary Island

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 attracted writers since 1983. Something about the island - the isolation, the warmth, the sense of being separate from America - drew writers who needed distance. The tropical light and colonial architecture provided setting; the tolerance provided space. Key West's literary heritage is real, not manufactured, though the writers themselves tended to arrive broken and leave (if they left) only slightly less so.

Mile Marker Zero

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 constantly. Fort Zachary Taylor offers the island's best beach and Civil War history. The Dry Tortugas National Park, 70 miles west, is reachable by ferry or seaplane. Old Town's Victorian houses, many converted to guesthouses, preserve 19th-century architecture. From altitude, Key West appears as the final island at the end of the Keys chain, where the highway ends, surrounded by water turning from Atlantic blue to Gulf green - the end of the road, where America stops and the Caribbean begins.

From the Air

Located at 24.56°N, 81.78°W at the southwestern end of the Florida Keys, 90 miles from Cuba. From altitude, Key West appears as the last island at the end of the island chain, the Overseas Highway visible crossing the water from the northeast, the compact Old Town visible, water surrounding in every direction. EYW airport occupies a portion of the small island. What appears from the air as an isolated island at the end of America is Key West - where Hemingway wrote, where the Conch Republic seceded, and where mile marker zero marks the end of the road.