Captain Tony’s Saloon in Key West is one of the most famous and historic bars in the Florida Keys, with a fascinating backstory that includes pirates, bootleggers, and even ghosts.
Origins & Early History
The building dates back to 1851 and originally served as an icehouse and morgue. During Key West’s early days, bodies from shipwrecks and local deaths were stored here before burial. Some say that ghosts of those souls still linger.
Later, the building became a variety of businesses, including a cigar factory, a bordello, and a speakeasy during Prohibition.
Captain Tony Takes Over
In 1958, local legend Captain Tony Tarracino bought the place and turned it into Captain Tony’s Saloon. Tony was a fisherman, gambler, bootlegger, and even the mayor of Key West (1989-1991). His colorful past and love for storytelling made him a Key West icon.
Famous Patrons & Connections
- Ernest Hemingway is rumored to have visited when it was called “Sloppy Joe’s” before the bar moved to its current location.
- Jimmy Buffett got his start playing music here, and his song “Last Mango in Paris” is about Captain Tony.
- Other famous visitors include Bob Dylan, Truman Capote, and even presidents like Harry Truman and John F. Kennedy.
Legends & Ghost Stories
- Hanging Tree: A large tree grows in the middle of the bar, said to be where 17 pirates and a woman accused of killing her husband were hanged. Some believe her spirit still haunts the place.
- Ghost Encounters: Many claim to have seen or felt paranormal activity inside, including unexplained noises and moving objects.
- Grave Marker Inside: There’s a tombstone in the bar floor belonging to a woman named Elvira, adding to the eerie atmosphere.
Present-Day Captain Tony’s
Today, the bar remains a must-visit spot in Key West, full of history, live music, and thousands of bras hanging from the ceiling (a tradition from past patrons). It’s one of the most unique bars in the U.S., offering a true taste of Key West’s wild past.
