The last island on the Overseas Highway, which hops by bridge down the Florida Keys from the mainland; Cuba lies under 150km away. Hemingway's house and wooden cottages fill an old town best toured by bike. December to April is the dry season; June to November brings hurricanes.
01Southernmost Point Buoy
A red, black and yellow concrete buoy hailing the continental US's southernmost point, with 90 miles to Cuba painted on it. By day the photo queue stretches dozens of metres, so come at sunrise. The true southern tip lies next door on Navy land.
Hemingway lived and wrote in this stone house in the 1930s, and dozens of six-toed cats roam the garden and rooms. They are said to descend from his own cat. The pool in the yard was the first on the island.
Every evening at sunset the wharf square on the western waterfront fills with jugglers, stalls and buskers for the sunset celebration. Performers start claiming their spots about two hours before the sun goes down.
Bars and shops crowd a street running about 2km across the island, and plenty of drinkers carry their cups from bar to bar. One end touches the Gulf of Mexico and the other the Atlantic. In late October the costume carnival Fantasy Fest packs the street.
A brick fort from the Civil War era shares the grounds with the island's best park beach. The shore is more crushed coral than sand, so water shoes help, and snorkellers find tropical fish along the rocks.
More than 110km west, Fort Jefferson, a hexagon of sixteen million bricks, sits on a tiny island. The only ways there are a daily ferry and seaplanes, and seats often sell out months in advance. The fort has no shop or snack bar, so bring drinking water.
The white wooden quarters on the naval station where President Truman came to work through his winters in office. His poker table and desk are still in place, and the inside is shown on guided tours only.
On the way to Key West the road runs almost 11km over open sea, beside the old bridge converted from a 1910s railway span. In 2022 the old bridge reopened to walkers and cyclists as far as Pigeon Key.
A cemetery in mid-island where many graves sit above ground, famous for jokey epitaphs. The best known reads I told you I was sick. The office at the gate hands out a map marking the famous stones.
About an hour north-east of Key West, the park has one of the few fine-sand beaches in the Keys. A broken span of the old railway bridge hangs over the sea, and its viewing deck shows the water in bands of colour. When parking is full, rangers send cars back.
After an 1846 hurricane toppled the old tower, this lighthouse went up farther inland in 1848. Climb 88 spiral steps to peer over the Hemingway Home's roof and across the island. The keeper's house below holds records of the families who tended the light.
A Civil War-era brick fort by the airport, now a museum of island history. Its star is Robert, a doll rumoured to curse people; the walls by his case are papered with apologies from visitors who photographed him without asking, then blamed him for bad luck.
Under a glass dome near Duval Street's southern terminus, dozens of butterfly species from around the world flutter overhead. Two flamingos stroll among the plants and a small waterfall. Wear bright colours and butterflies often land on you.
It shows the haul of Mel Fisher, who hunted 16 years for the Spanish treasure galleon Atocha, sunk off Key West in 1622, before finding it in 1985. Gold bars, emeralds and silver coins fill the cases. One gold bar is set out for you to lift by hand.
On Big Pine Key, about 50km northeast of Key West, live the Key deer, which grow no bigger than a large dog. Around the refuge's pond and woodland trails they are easy to meet early or near sunset. Feeding them is illegal, and drivers must slow down.