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North America / USA / Florida / South Florida / The Keys / Key West / Best Nightlife

Sloppy Joe’s

You’ll have to stop in here just to say you did. Scholars and drunks debate whether this is the same Sloppy Joe’s that Hemingway wrote about, but there’s no argument that this classic bar’s early-20th-century wooden ceiling and cracked-tile floors are Key West originals. There’s live music nightly. Also check out Joe’s Tap Room, a separate bar within the complex that serves an excellent selection craft beers.