The southernmost city in the continental United States is, in fact, an intimate six-square-mile island that feels like a Caribbean getaway. Key West was the lone city south of the Mason-Dixon to remain with the Union during the Civil War. To this day, that freethinking sensibility remains intact, and the city’s location—closer to Cuba than to Miami—results in an eclectic cultural mix. This is a place where people go barefoot, chickens roam the streets, and epitaphs like DEVOTED FAN OF JULIO IGLESIAS are found in the cemetery. Though it may be best known for Hemingway and Jimmy Buffet’s Margaritaville, you’ll ﬁnd the real essence of the place in its very particular style of Victorian and Queen Anne architecture, and in its eclectic residents: quirky but classic, and ready to welcome everyone.
Catching a cabaret performance (think: men in drag impersonating celebrities) at La Te Da.
Taking a memorable 30-minute tour of Ernest Hemingway’s tropical home led by a group of stand-up comics-turned-literature lovers.
Stopping by the Blond Giraffe for authentic key lime pie. (Order it topped with meringue!)