Sloppy Joe's

You'd be hard-pressed to learn about Key West without hearing of the infamous Sloppy Joe's bar, where people come to get, well, sloppy. It was Hemingway's favorite watering hole ("Sloppy Joe" was Captain Joe Russell, the founder and one of Hemingway's drinking buddies) and remains a popular place for pub grub and live music. In fairness to historical accuracy, Hemingway probably spent more time haunting the original location (formerly a speakeasy and now Captain Tony's) until 1937. But the walls are filled with photos and memorabilia devoted to the author, and it overflows with "Papa" doppelgangers during Hemingway Days each July. Attached to the main bar is Joe's Tap room, with several craft beers on tap. By nightfall, this place starts to get rowdy, and the tables are cleared away to make room for dancing.