Captain Tony's Saloon

After you’re done at Sloppy Joe’s, walk across the street to Captain Tony’s if you love a historic bar with a juicy backstory. This was actually the original Sloppy Joe’s, but legend has it that after a landlord dispute, the bar and its regulars packed everything up in the middle of the night and walked it across the street to the new Sloppy Joe’s. (Hemingway apparently thought this was hilarious). Captain Tony’s isn’t as energetic as Sloppy Joe’s, but it’s one of those old dark bars wallpapered in wrinkly dollar bills that feels so uniquely Key West. Ask the bartender about the building’s history as the city morgue if you’re feeling brave.