Capt. Tony’s Saloon

Captain Tony’s Saloon in Key West isn’t just a bar—it’s a story in wood, ghosts, and rum. Before it became a saloon, the building served as an icehouse, morgue, and city gallows. A tree still grows through the roof, once used to hang condemned criminals. Bones have been found beneath the floorboards, and the staff casually report ghostly sightings between drinks.

From 1933 to 1937, this location was home to the original Sloppy Joe’s—a favourite haunt of Ernest Hemingway. After the bar moved, it became Captain Tony’s in the 1950s and quickly earned its own legacy. Several of the barstools are dedicated to guests who once visited, including Ernest Hemingway, Truman Capote, Jimmy Buffett, Shel Silverstein, John Prine, John F. Kennedy, and Harry Truman.

The walls and ceiling are decorated with dollar bills, signed bras, license plates, and notes from travellers around the world. The bras come in all sizes—A-cup, B-cup, C-cup, D-cup, and DD-cup—adding to the irreverent, welcoming vibe. You called it a “trivelig sted,” and it truly is—despite the ghost stories and gallows tree looming overhead.

Captain Tony’s is part roadside attraction, part sacred dive. It’s a place where the line between history and legend blurs, and the ghosts are just as likely to be tourists as the dearly departed.