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.

Discover Key West beaches such as South Beach, Dog Beach or Higgs Beach or landmarks such as Key West Lighthouse, Casa Antigua, Mallory Square and the southernmost point in the continental U.S.

Accommodations in Key West are plentiful and run the scale from top end to economy. There are large and small hotels and motels, inns and guesthouses. The best thing to do is think about what you want from your vacation and how best to accomplish that, with consideration for who will be accompanying you.