Captain Tony's Saloon

The building started as an icehouse and morgue in 1851, then became a telegraph station, cigar factory, bordello, and speakeasy. Hemingway drank here from 1933–1937 when it was still called Sloppy Joe's.

Captain Tony's Saloon at 428 Greene Street in Key West occupies one of the most historically macabre buildings in Florida. Built in 1851 as an ice house--the coolest spot in town--it doubled as the city morgue until the 1890s.

A massive tree grows through the center of the building, its branches extending through the roof. This is the original hanging tree, used for public executions in what was then an open courtyard. At least 75 people were hanged here for piracy and other crimes, including one woman: a local resident who murdered her husband and two sons, then waited in her house wearing their blood-soaked blue dress until police arrived. She was hanged immediately, and the "Lady in Blue" has haunted the building ever since, her spectral image captured in photographs by countless visitors.

In 1865, a devastating hurricane washed corpses from the morgue out to sea--all except one, which was recovered and buried beneath the building, surrounded by holy water. During 1980s renovations, workers discovered bones from eight to fifteen additional bodies. A skeletal hand now hangs behind the bar as a reminder.

The building served as a wireless telegraph station during the Spanish-American War, receiving the news that the battleship Maine had been destroyed in Havana harbor. It later became a speakeasy, bordello, and cigar factory.

In 1933, Josie "Sloppy Joe" Russell opened his bar here--the original Sloppy Joe's where Ernest Hemingway spent countless evenings from 1933 to 1937. Tony Tarracino bought it in 1958, and singer Jimmy Buffett got his start here in the '70s, later immortalizing Tony in "Last Mango in Paradise."

Patrons report pockets of freezing air, strange noises, and the feeling of being watched. The women's bathroom is particularly active--doors lock on their own, and visitors describe overwhelming unease.