The Florida island Hemingway called ‘the best place I’ve ever been’
Nearer to Havana than Miami, Key West’s vibe is famously chill.
Sunrise over Key West, the island where Ernest Hemingway wrote (or started) some of his most famous work.Credit: Alamy
Key West, Ernest Hemingway once groused, was “Saint Tropez for the poor”. In the spring of 1928, the novelist had tired of Paris and moved to its opposite, a Florida island on the Gulf of Mexico. Just six kilometres long, two kilometres wide and, if you’re Diana Nyad, a 52-hour swim from Cuba, Hemingway wound up writing three-quarters of his oeuvre drunk on Key West’s seedy, beachy vibe.
In To Have and Have Not, later turned into a movie with Humphrey Bogart, Hemingway writes in fonder terms of the place: its “dark blue Gulf water”, creaky fishing boats and schools of small fish, “oval-shaped, golden-coloured, with faint purple stripes”. After a loan from his then-wife’s uncle afforded a splendid two-storey home made of quarried coral, the future Nobel Prize winner’s tone was enamoured. “It’s the best place I’ve ever been anytime, anywhere,” he declared in a letter to a friend from a cigar maker’s raffia chair in his pool house. “Flowers, tamarind trees, guava trees, coconut palms … Got tight last night on absinthe and did knife tricks.”
Key West’s main drag, Duval Street, still buzzes with the profane machismo of its most famous regular. (That’s especially true when the annual Hemingway lookalike contest rolls around.) From noon well into the humid night, dives sling rum runners (made with blackberry and banana liqueurs) while on the rooftop of the Bull and Whistle pub, clothing is optional.
Duval Street, the island’s main drag.Credit: Getty Images
Meanwhile, Hemingway’s former house is a museum and retains many quirky features. A gang of six- or seven-toed polydactyl cats descended from the author’s pet Snow White roam a luxurious garden of Indian banyans, date palms and African sandbox trees; a urinal wrenched from nearby Sloppy Joe’s Saloon functions as a birdbath. (The story goes that the bar bestowed it on the author because he pissed his fortune away there.)
Along with pirates from the Caribbean, bootleggers, bohemians and Bahamians, other writers have been drawn to this romantic outpost over the years. These include the poet Elizabeth Bishop, who found respite in the tropics from a confined New England childhood, as well as Wallace Stevens, Ralph Ellison, Tennessee Williams and Judy Blume, who runs a bookshop in town.
Latterly, Key West’s image has been shaped by another singular scribe: Jimmy Buffett, the singer-songwriter who decamped from Tennessee in his 20s and whose biggest hit, Margaritaville, has served as soundtrack to countless salt-rimmed evenings. Buffett’s 1973 single, I Have Found Me a Home, encapsulates Key West’s escapist appeal: “The days drift by / They don’t have names / And none of the streets here look the same.”
Buffett is correct that the streets, though in a beachside town, are Key West’s most interesting aspect. Many of the structures in the Old Town area date from a spectacular boomtime in the late 19th century, when – thanks to the lucrative business of salvaging wrecked ships – it was the wealthiest city per capita in the United States. An equally spectacular bust followed. The US Navy shut up shop; the cigar industry was lured to nearby Tampa; and, in 1935, the railway which connected the town to the mainland was swept away. A tour on the Conch Train, pronounced “conk” and named after the mollusc which is Key West’s unofficial mascot, reveals unique architectural details. One such ingenious feature seen on Elizabeth Bishop’s house is the “eyebrow” roof, which extends to shade second-floor windows.
Descendants of Hemingway’s six-toed cat, Snow White.Credit: Getty Images
If you ignore the first “winter White House” – president Harry S. Truman’s hideout – and focus on the pastel cottages and palm trees, it’s possible to imagine this is not the US at all. As John F. Kennedy noted during the 1962 missile crisis, Key West is only “90 miles from Cuba” – and it’s closer to Havana than to Miami. At one point, half the residents were of Cuban origin. Just outside town is the southernmost point of the continental US, a natural endpoint for marathon swims. Nyad set a record in 2013 when she was the first to swim the Florida Strait without a shark cage or flippers.
In 1997, Australia’s Susie Maroney also completed the journey and, once on shore, might have thought the coastline looked familiar: it’s lined with casuarinas. But an Australian probably wouldn’t think the beaches worth lingering on. The sand is sparse and sharp with crushed coral, while the shallows teem with seaweed. Best to follow Hemingway’s lead and head out on a fishing boat instead, for snapper, bonefish and tarpon.
Afterwards, a slice of key lime pie is a must. The Chamber of Commerce once said that 70 per cent of all visitors to Key West had at least one piece. (The other 30 per cent had probably drunk too many rum runners.) Key lime trees, whose fruit is smaller and more aromatic than the Persian kind, came to the area with migrating Haitians in the early 1800s.
Today, most key limes in Florida originate in Haiti because successive hurricanes have hit local groves hard. Perhaps it’s this threat of everything being wiped away – and the increasing intensity and frequency of hurricanes in recent years – that makes Key West so fun. “Relax, you’re on island time now,” a server implored on my first night there. The setting sun was as luridly coloured as my rum punch, and so I did.
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