Ernest Hemingway Home and Museum

The Hemingway Home is Key West's most famous address and earns it. Ernest Hemingway and his second wife, Pauline Pfeiffer, lived in this limestone Spanish Colonial house on Whitehead Street from 1931 to 1939 — Pauline's uncle bought it for them — and the decade here was among the most productive of his life: he wrote much of Green Hills of Africa, The Snows of Kilimanjaro, The Short Happy Life of Francis Macomber, and To Have and Have Not, his one novel set in Key West, in the studio above the carriage house reached by a catwalk. The house is furnished with family pieces and the trophies and souvenirs of his African and Spanish years, and the guided tours — included with admission, leaving every few minutes — are the reason to come: the docents are storytellers, and the stories (the boxing ring, the bar urinal from Sloppy Joe's, the pool) are better than the furniture. The pool is the legend: built in the late 1930s for around twenty thousand dollars, by far the most expensive thing on the property, it prompted Hemingway to press a penny into the wet concrete as his "last cent" — the coin is still there. And then there are the cats: some fifty-plus live on the grounds, about half of them polydactyl, with six toes or more, said to descend from Snow White, a white six-toed cat given to the family by a ship captain. They sleep on the beds, patrol the gardens, and have their own cemetery and on-call vet. Even visitors who have never read a word of Hemingway leave charmed.

The property predates its famous tenant by decades: the lot was bought in 1851 and the house built in the second half of the nineteenth century from limestone quarried on the property itself, which left it with a rare island basement and some of the thickest walls in town — it has come through every hurricane since, including Irma in 2017 and Ian in 2022, with the cats safe. When the Hemingways arrived it was a near-ruin; Pauline restored it into the airy, high-ceilinged house you see, with the garden that is now the cats' kingdom. Hemingway left in 1939 for Cuba and his third marriage; Pauline stayed until her death in 1951, and the house was sold at auction in 1961 and opened as a museum in 1964. It was designated a National Historic Landmark in 1968, and it remains privately owned and operated — which explains the old-fashioned, personality-driven tour style.

Visiting well: doors open in the morning and the first hour is the calmest; by late morning the Conch Train, trolley, and cruise-day crowds converge and tours run large. The guided tour runs about half an hour and covers the main house, then you are free to wander the grounds, the pool, the writing studio (viewed through a protective grille), the bookshop, and the cat cemetery at your own pace. Allow an hour in total, more if you are a cat person, which you will become. The cats are free to roam and allowed to be petted gently if they approach you; they are not to be picked up, and the staff are serious about it. Check current hours and admission on the museum's own site before you go — and note that the house closes for hurricane threats like everything else on the island.

Context makes the visit richer. Across Whitehead Street stands the Key West Lighthouse, whose tower Hemingway is said to have used as a landmark to find his way home from the bars — climb it after for the view down onto the Hemingway garden. Sloppy Joe's and Captain Tony's on Duval carry the drinking half of the legend; the Hemingway Days festival in July brings the lookalike contest that is exactly as surreal as it sounds. Readers should pick up To Have and Have Not before the trip: its Depression-era Key West of rumrunners and charter captains is still partly visible in the harbor and the side streets, and reading it here, a block from where it was written, is one of the island's quiet pleasures.