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Few American cities wear their mythology as openly as Key West. Perched at the end of a 113-mile chain of islands that trails south-west from the Florida mainland, this small coral island sits closer to Havana than to Miami, and that geographical fact has shaped everything from its architecture to its attitude. The old Conch Republic spirit, a half-serious declaration of independence from the United States in 1982, still colours the way locals talk about their home, and first-time visitors tend to feel the shift in register the moment they cross the Seven Mile Bridge.

Duval Street is the obvious spine of the old town, running from the Gulf of Mexico to the Atlantic in under a mile, and the wooden shotgun houses and Bahamian-influenced architecture along its side streets reflect a building tradition that predates Florida statehood. The Historic Seaport district, where the shrimping fleet once made Key West one of the wealthiest cities per capita in the country, now draws visitors to its docks and waterfront bars. Mallory Square, at the north-western tip of the island, has hosted the nightly sunset celebration for decades, a loose gathering of street performers and spectators that functions as an unofficial civic ritual.