Captain Tony’s Saloon, A Chilling Experience

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Photo by Toni Cuenca on

Back in the 1850s, the building that now houses the ever so popular Key West watering hole called Captain Tony’s Saloon, was once an ice house and the city’s first morgue.

Perhaps the most unusual thing that one would notice right off the bat when visiting the Saloon is the large tree growing right through its center. The tree is known as “The Hanging Tree,” and it’s legend dates back to when the tree was supposedly used to execute pirates and one woman.

The woman executed there is known as “The Woman in Blue,” and she was executed for murdering her entire family. She was named for the blue dress she wore, and it is said that she still walks the premises.

Then there is Elvira, a woman who supposedly was found dead there after the hurricane of 1865. As the legend goes, when the unidentified woman was found, a wall was built around her remains and holy water placed inside. In the 1980s, during renovations and an expansion, skeletal remains were found along with a headstone with the name Elvira on it. The headstone remains in the bar to this day.

The building has a long history, and after its days as an Ice House, it became the original location of the famous Ernest Hemingway hangout, Sloppy Joes. After a dispute with the landlord, Sloppy Joe’s moved around the corner to its current location.

After the Sloppy Joe’s days, the building served other purposes, from a cigar factory to the location of several speakeasies to even a telegraph station to now it’s the current purpose, the location of Captain Tony’s Saloon.

Patrons and employees of the popular saloon have reported many creepy experiences, like doors that open and close by themselves or lock and unlock without explanation. Employees have heard voices without anyone else being in the building with them. Many people have claimed feeling cold spots in the hallways and in the ladies’ restroom.


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