Sloppy Joe's is the bar that Hemingway supposedly frequented in the 1930s — though the connection is complicated by the fact that the bar has moved locations and the original establishment is now Captain Tony's Saloon a few blocks away. Historical accuracy aside, Sloppy Joe's has made itself into Key West's most famous bar through sheer persistence and a permanent live-music lineup.
The bar is open, loud, and lively from noon until late. The music is generally rock and blues covers; the drinks are strong and the prices are tourist-standard. It sells a lot of merchandise. None of that is the point — the point is the atmosphere, the ceiling fans spinning above the crowded tables, the open walls letting in the warm air, and the sense that you are participating in a Key West tradition, however commercialised it has become.