Sloppy Joe's

This is the most famous, crowded, and historic bar in Key West. And yes, it’s worth stopping in for a frozen rum runner. Sloppy Joe’s is such an institution because Hemingway himself spent many years here drinking way too much and probably getting into a lot of fights. Today, it’s a little tamer, undeniably touristy, but still fun if you don’t mind big, loud bars. There are usually live bands playing cover songs that are easy to scream along to (a man named Gerd Rube was crushing it during our last visit). But if you want to avoid the more rambunctious Duval Street crowds, go around lunch (or check the bar’s live webcam before you go). Also, if you happen to be visiting around July 18, please come here for the annual Hemmingway look-alike contest.