Sloppy Joe’s
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Sloppy Joe’s

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 for the title. The casual saloonlike atmosphere is complemented by potent drinks—served from 9 a.m. until the wee hours (except Sundays, when they're served from noon on)—as well as live music.

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