Captain Tony's Saloon
Built around 1851, this building served as an icehouse and the city morgue, then housed the original Sloppy Joe's Bar that Ernest Hemingway frequented before becoming Captain Tony's Saloon in 1958. A large tree grows up through the center of the bar, the old hanging tree where, by local legend, condemned prisoners and pirates were executed. When the floor was worked on, human remains were reportedly uncovered, and grave markers remain embedded in the floor today. The most told ghost is the Lady in Blue, said to be a woman hanged from the tree after being accused of murdering her family, found in a blood-soaked blue dress; patrons report her figure near the tree and unease in the women's restroom. Staff and guests describe cold spots, unexplained noises, and the sensation of being watched, making it one of Key West's most visited haunted bars.
📍 428 Greene St, Key West, FL 33040, Key West, FL · Get directions