Captain Tony's Saloon

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 Duval. 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 early nineteenth century. Visitors will notice that inside the bar is a large tree- this was the gallows tree in the open courtyard that was used for judgements, and the building was later built around it.  At least 75 people were hung here for piracy, along with other transgressors. Ironically, the tree itself is still alive; it extends through the roof, though Hurricane Irma took much of the top, at least six inches of tree still peek above the building. Curiously, it still sprouts twigs and leaves inside the dusky bar.

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 floorboards were taken up to reveal the bones of between 15-18 people. Among them, a gravestone for a young woman named Elvira Drew was discovered. Elvira was married, in her mid-teens, to an abusive, alcoholic man in his fifties. Elvira left the world in 1822 at the tender age of 19, hanged on winter solstice nearly two hundred years ago for killing her husband- self-defense wasn’t a valid argument at the time. Her tomb marker now sits beside the pool table for eternity, or at least until the bar undergoes another renovation.

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”.

There are far more bodies under the floor than there are gravestones- some graves are flush with the current floor level, and some rest beneath it. So wherever you step, you’re walking on someone’s grave. And before you leave, make sure to say goodbye to the resident skeleton, now propped up and fashionably dressed inside the bar.