Key West

Most visitors see Duval Street and think they've seen Key West. Duval is about eight percent of it. The island that rewards attention is the one two blocks either side: lanes of nineteenth-century wooden houses built by ships' carpenters, roosters in the road, cemetery humor, and a town that has spent two hundred years being unlike anywhere else in the country.

How it got this way

Four histories stacked on one small island, and you can see all of them in an afternoon.

The wreckers. In the 1830s Key West was the wealthiest city per capita in the United States, built on the legal, court-regulated salvage of ships wrecked on the reef. Old Town's architecture is that money. The full story →

Cuba and cigars. Key West is the closest American city to Cuba, and from the 1830s onward Cuban immigrants arrived in numbers, bringing cigar-making with them. At its peak the island produced over 100 million cigars a year. José Martí visited repeatedly in the late 1800s, raising support among the exile community for Cuban independence.

The railroad. On January 22, 1912, Flagler's first train arrived, connecting the island to the mainland for the first time. The full story →

The collapse and the artists. By the 1930s the cigar industry had gone to Tampa, sponging had failed, and the city was effectively bankrupt. What it had left was cheap rent and extraordinary light — which is precisely what drew Hemingway, and later Tennessee Williams, Elizabeth Bishop, and Robert Frost.

Old Town

The historic district holds one of the largest concentrations of surviving nineteenth-century wooden architecture in the United States — well over two thousand significant structures. Walk it. The details are the point: gingerbread trim cut by ships' carpenters, widow's walks, louvered shutters, Bahamian roof lines built to shed hurricane wind, and eyebrow houses with the upper windows tucked beneath the roof overhang for shade.

• Ernest Hemingway Home & Museum — 907 Whitehead Street, the six-toed cats, the penny in the pool deck. Full guide →
• Key West Lighthouse — across the street from Hemingway's house; climb it for the best view over Old Town.
• Truman Little White House — Harry Truman spent 175 days here across eleven visits, running the country from a former naval commandant's quarters.
• Key West Cemetery — nineteen acres of above-ground vaults and the best epitaphs in America. The famous one reads "I told you I was sick."
• San Carlos Institute — founded 1871 by Cuban exiles; the building where Martí organized. Small, free, and historically enormous.
• Mel Fisher Maritime Museum — the Atocha treasure, recovered after a sixteen-year search.

Mallory Square and the sunset

The nightly Sunset Celebration is genuinely old — it grew organically in the 1960s and became an institution: jugglers, fire eaters, a man with trained cats, and a few hundred people applauding the sun going down. It's touristy and it's also real, and the performers are largely the same ones who've been doing it for decades.

If the crowd isn't for you, the alternatives are better anyway: the pier at the end of White Street, Fort Zachary Taylor beach, or a sunset sail out of the Historic Seaport, which puts the whole harbor between you and the noise.

Fort Zachary Taylor

The best beach on the island, at the end of the Truman Annex — deep water close in, actual shade from Australian pines, and a Civil War-era brick fort behind it. Key West stayed under Union control throughout the Civil War even after Florida seceded, and this fort is why. Snorkeling off the rocks here is surprisingly good.

Mile Marker 0

The green sign at the corner of Whitehead and Fleming marks the southern end of U.S. 1 — a road that runs from here to the Canadian border in Maine. The other essential sign is the concrete buoy at South and Whitehead marking the southernmost point in the continental United States, ninety miles from Cuba. There's a line for the photo, always. It's worth it once. How mile markers work →

The Dry Tortugas

Seventy miles further west, reachable only by ferry or seaplane: Fort Jefferson, an enormous unfinished nineteenth-century brick fortress on a speck of sand, surrounded by some of the clearest water and healthiest coral in North America. It's a full day and it needs booking well ahead. For many visitors it ends up being the best day of the trip.

One more thing

Ask a local where they're from and if the answer is "I'm a Conch," they mean they were born here — and if they say "freshwater Conch," they mean they've lived here long enough to count. It's the same word behind the flag on every third storefront, the one from the day this island seceded from the United States and won.