Key West

The Overseas Highway is the kind of road you take slowly on purpose — 180 kilometres of bridges leapfrogging from island to island, the Atlantic on one side, the Gulf on the other, water so many shades of blue it embarrasses paint charts. By the time Lia and I reached the end of it in Key West, we had that giddy, sun-struck feeling of having driven off the edge of the map. And in a sense you have: this is the southernmost point in the continental United States, a fact marked by a fat concrete buoy that people queue up to photograph. But the buoy isn’t the point. The point is the mood — loose, tropical, faintly ridiculous — that settles over you the moment you park the car and start wandering the shaded lanes of Old Town.

Old Town and the writers’ ghosts

We spent our first day simply walking the Old Town, and it is one of the most beautiful collections of houses I’ve seen in America — Conch cottages and captains’ mansions in sherbet colors, wrapped in white gingerbread trim, half-swallowed by bougainvillea and palm. Roosters, feral and loud, strut everywhere as though they own the place, which more or less they do. We toured the Hemingway Home, where the man wrote in a studio over the garden and where his famous six-toed cats still doze on every porch and bed — Lia counted eleven of them before giving up. Down the street the little brick lighthouse offered a climb and a view over the whole tin-roofed town to the encircling sea.

Duval Street and the water

Duval Street runs the length of the island and is Key West at its most unbuttoned — bars, buskers, drag shows, T-shirt shops, and the historic Sloppy Joe’s where Hemingway drank. We did a lazy afternoon of it, ducking into a shaded courtyard for key lime pie so tart it made Lia’s eyes water, then escaped the crowds by heading to the water. We snorkeled out at the reef on an afternoon boat — the only living coral barrier reef in the continental US — drifting over parrotfish and swaying sea fans in bathtub-warm water. Back on land, we walked out onto the old Truman Waterfront and watched pelicans crash-dive off the pilings while shrimp boats came in.

The sunset ritual

Every evening, without fail, the whole town migrates to Mallory Square for the Sunset Celebration, and I mean that literally — it is a nightly festival that has run for decades. Jugglers, a man with performing house cats, a bagpiper, fire-eaters, and vendors of conch fritters all set up as the crowd thickens along the waterfront. Lia and I found a spot on the seawall, bought a plastic cup of something frozen and rum-based, and joined the strange communal vigil. And then the sun did its thing, sliding fat and orange into the Gulf, the sky going pink and violet, sailboats crossing black against it. When the last sliver vanished, the entire square burst into applause — for the sun, for the day, for the sheer daft joy of it. We clapped too.

Getting There

Key West has its own small international airport with flights from Miami, Orlando, and a handful of other cities, which spares you the long drive. But the drive is half the experience: the Overseas Highway (US-1) runs about three and a half to four hours from Miami, threading the entire chain of the Keys, with the famous Seven Mile Bridge as its centerpiece. Once you arrive, ditch the car — Old Town is compact, flat, and made for bikes, scooters, and the town’s slow-cruising trolleys. Parking is scarce and the whole island can be crossed on foot in an afternoon.