Sloppy Joe's

Sloppy Joe's is a two-story establishment at the corner of Greene and Duval Street in Key West, featuring a long bar counter, several seating areas, and walls covered with old photographs. The space offers tables and bar stools where guests can sit for drinks and meals while live bands perform on a small stage near the entrance.

The bar opened on December 5, 1933, the day after Prohibition ended, in a different downtown building. A rent increase forced the move to its current address in 1937, where it has remained in continuous operation ever since.

The name comes from a former establishment in Havana that founder Joe Russell admired and adopted for his new bar in Florida. The interior walls display old photographs and memorabilia from the decades when it served as a meeting point for writers and sailors.

The bar opens daily at 10 AM and closes at 2 AM, serving drinks, sandwiches, and hosting live music throughout the day and evening. Visiting in the morning or early afternoon offers a quieter experience, while evenings bring crowds and louder performances.

Every July, the bar hosts a contest where bearded men compete in multiple rounds to resemble the famous writer who frequented the place. The event draws participants from across the country and fills the bar and surrounding streets with hundreds of spectators.