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907 Whitehead St, Key West, FL 33040, USA

Key West’s most famous literary resident, Ernest Hemingway, lived in this two-story Spanish-colonial villa for nearly a decade and composed several of his best-known works here. His second wife, Pauline, insisted they add a pool to the...

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220 Simonton St, Key West, FL 33040, USA

New Orleans may be home to America’s most festive thoroughfare, Bourbon Street, but Key West’s Duval Street is a close second. This two-kilometer-long (1.25-mile-long) road runs from north to south, from one end of the island to the...

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201 Duval St, Key West, FL 33040, USA

No place is quite as synonymous with the Key West spirit as Sloppy Joe’s, which has been around since 1933 and was a regular hangout for Ernest Hemingway; the bar even hosts an annual Papa look-alike contest, with white-bearded men competing...

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429 Caroline St, Key West, FL 33040, USA
In the land of piña coladas and light beers, The Other Side cocktail lounge is chiseling out new booze territory one ice globe at a time. Drinks, loosely inspired by the Keys, are like nothing else on the island. There’s the frothy...
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113 Fitzpatrick St, Key West, FL 33040, USA

Founded in 1984, this is the oldest cigar factory operating in the Keys, and it uses traditional Cuban methods to cure and roll its stogies. You can choose from a large selection of cigars and also watch a skilled torcedor (cigar roller) in...

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711 Duval St, Key West, FL 33040, USA
When you want some seriously campy fun, Aqua is the place to go. Join the (very mixed) crowd for dancing, nightly drag shows that feature the Aquanettes, and karaoke Monday through Thursday. If you want something a touch more low-key, there's the...
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400 Wall St, Key West, FL 33040, USA

Key West is billed as "the Home of the Sunset," which means every time the sun sinks below the horizon, it’s time for a party. Since the 1960s, Mallory Square’s dock has been hosting this nightly celebration, which begins two hours...

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806 Caroline St, Key West, FL 33040, USA

Old-school Key West at its best—this steak house and seafood spot near the waterfront has been around since 1909. The fun, funky atmosphere with lots of wood and a mishmash of nautical memorabilia has a laid-back vibe, and you can dine...