Located at the end of the Florida Keys, Key West America’s southernmost city has the vibe of a colorful Caribbean outpost with a dash of New Orleans high life. It’s a fun-loving, heavy-drinking town with a lot of history, more than a little touristy goofiness, and a large gay community.

Cruise ships dock on the Gulf side of the island, at Mallory Square (Old Town’s tourist central), the nearby Hilton Resort’s Pier B, or the U.S. Navy base’s Outer Mole pier. Most cruise lines offer guided walking tours and bike tours, but this is really a port to explore on your own, with most attractions in easy proximity to the cruise docks. Wander around touristy Mallory Square and Duval Street, check out some of the theme bars, and then take a walk down some of the quieter side streets. Or, you might want to spend your day playing golf, diving, snorkeling, or in the spirit of former Key West resident Ernest Hemingway deep-sea fishing.

Iconic sight The Hemingway Home on Whitehead Street ( ) is where Papa lived in the 1930s, writing For Whom the Bell Tolls and A Farewell to Arms in his studio out back. bottoms up Bars are an essential part of the Key West experience. Two storied but touristy bars Sloppy Joe’s on Duval Street and Captain Tony’s Saloon on Greene Street compete for bragging rights to the hard-drinking Hemingway legend. Wherever you end up, try some of the favorite local beer, Hog’s Breath, or the favorite local rum, Key West Gold.

Slice of history On Front Street, the Harry S Truman Little White House ( ) was Truman’s vacation home during his presidency and today remains just as he left, it, decorated in late-1940s style. smell the roses Lush tropical gardens surround The Audubon House ( ), a restored 19th-century sailor’s mansion filled with engravings by famous naturalist and artist John James Audubon. for nature lovers On the waterfront at Mallory Square, the Key West Aquarium ( ), opened in 1932, displays marine creatures native to the Keys, from sea turtles and jellyfish to alligators and stingrays.


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