Key West
Key West sits ninety miles from Cuba at the end of a hundred-and-thirteen-mile highway built on the piers of a railway the 1935 hurricane destroyed, and it has been a wrecking port, a cigar town and a writers' refuge in turn. Bicycles beat cars here; see Hemingway's house early, and give the last hour of the day to Mallory Square, where sunset is a municipal event.
Why go
The end of the road — US 1 runs a hundred and thirteen miles over water and stops here. Hemingway's house — where he wrote for eight years, with the six-toed cats still in residence. Closer to Havana than to Miami — ninety miles south, and the culture shows it. Sunset as a municipal event — Mallory Square, nightly, with jugglers and a crowd.
The character
Key West was the wealthiest city per capita in the United States in the 1830s, on the proceeds of wrecking — salvaging ships that ran onto the reef, a licensed and lucrative business until lighthouses ended it. Then came cigars, made by Cuban exiles, and sponges, and then nothing much: by the Depression the town was bankrupt and half-empty, which is when the writers arrived because it was cheap.
Hemingway bought the Whitehead Street house in 1931 and wrote To Have and Have Not and much else there over eight years. Tennessee Williams came in 1941 and stayed thirty years; Elizabeth Bishop, Robert Frost and Wallace Stevens all worked here. What produced that concentration was isolation and cheapness, and neither survives — the island is now expensive and busy. But the physical place remains: wooden conch houses with tin roofs, a hurricane history written into every building code, and a self-consciously eccentric municipal culture that once declared independence as the Conch Republic over a road block.
Places of character
Hemingway House — the writing studio over the carriage house, and around sixty polydactyl cats. Southernmost Point buoy — a painted concrete marker, permanently queued, and ninety miles from Cuba. Key West Cemetery — above ground because of the water table, with famously sardonic epitaphs. Truman's Little White House — where the president spent 175 days of his term. Mallory Square at sunset — the nightly gathering; genuinely good street performers among the schlock. Dry Tortugas — a nineteenth-century fort seventy miles further west, reachable by seaplane or ferry.
The way to do it
Cycle — the island is four by two miles and flat, and parking is punitive. Do Hemingway's house early. Go a day to Dry Tortugas if you can; it is the best thing in the Keys and most visitors never make it. And drink somewhere without a T-shirt shop attached.
One perfect day
Coffee and a cycle around the island before the heat — the cemetery, the conch houses, the harbour. Hemingway House at opening, standing in the studio with the typewriter and the cats. Cuban lunch on Duval's quieter end. Afternoon on the water: a snorkel over the reef or the seaplane out to Dry Tortugas if the day allows. Back for Mallory Square at sunset with the jugglers and the crowd. Dinner of hogfish, then a bar with music and no theme, of which several survive.
Grand hotels
Casa Marina — Flagler's 1920 hotel on the only real beach, built as the terminus of his railway. The Marquesa — four restored 1884 conch houses around two pools, and the island's quiet address.
When to go
Best expression: December to April — dry, warm, and the reef at its clearest. Consider: January for the literary seminar, which draws serious writers. Avoid if possible: August to October, the hurricane peak, and Fantasy Fest in late October unless that is the plan.
The frame
Ideal stay 3 nights · Minimum 2 nights · Best arrival the drive down the Overseas Highway, or fly in · Airport EYW, 4 km · Walkability total, by bicycle · Best without a car yes, once you are there