Most trips to Key West involve a visit to its most famous bar on Duval Street, Sloppy Joe's, but for those who would like a little literary history and a whole bunch of morbidity with their cocktail, the "Sloppy Joe's" where Ernest Hemingway used to sit and drink is right around the corner on Greene Street, now known as Captain Tony's Saloon.
Josie Russell opened Sloppy Joe's on Greene Street in the 1930s, and in 1938 when the rent was raised by a dollar a week, the bar moved to its more famous location on Duvall. The building that was once Hemingway's watering hole went through several incarnations before finally being purchased by Captain Tony Tarracino and Captain Tony's saloon was born.
The building itself has a long and macabre history, stretching back to the 1850s. Visitors will notice that inside the bar is a large tree that the bar is built around. Now a delightful natural centerpiece, in the 1800s it was used as the town hanging tree. At least 75 people were hung here for piracy.
In its storied past, the building saw time as a morgue, a bordello, a telegraph office, a speakeasy and a cigar factory. During refurbishing work in the 1980s, the floor boards were taken up to reveal the bones of between 15-18 people. Among them, a gravestone for a young woman named Elvira Edmunds was discovered. Miss Edmunds left the world in 1822 at the tender age of 21, her tomb marker now sits beside the pool table for eternity, or at least presumably until the bar changes hands again.
Another gravestone in the bar underneath the old hanging tree belongs to Reba I. Sawyer, a Key West native who lived from 1900 to 1950. Upon her death, her husband found scandalous letters between his wife and another man. The letters detailed their trysts, and how they would arrange to meet at Captain Tony's Saloon. The widowed husband dragged his cheating partner's tombstone from the cemetery into the bar, placed it under the tree, and supposedly said "this is where she wanted to be, so this is where she will stay".
Know Before You Go
Down the street from the famous Sloppy Joes.