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Captain Tony's of Key West: Florida's most notorious saloon

Captain Tony's is famous for hosting Jimmy Buffett and Hemingway, but it has a dark, infamous past full ghosts, dead bodies, and even a hanging tree...

Few bars in America have a history as storied as Captain Tony’s in Key West. The barstools here have propped up famous folks like Ernest Hemingway, Shel Silverstein, and even Presidents Kennedy and Truman. Heck, Jimmy Buffett even got his start in Key West on the stage of Captain Tony’s, but this legendary bar has a history of death and mystery unlike any bar in America.

Captain Tony’s eerie past started in the mid-1800s when the building first housed the city’s morgue. The morgue had a bit of bad luck in 1865 when a hurricane decimated the Keys and bust up the building, sending dead bodies floating through the floodwaters.

When the storm cleared, only one of the bodies was recovered. Legend says they buried the one body and built a wall around it with vials of holy water. These days, it’s less of a cemetery but instead the billiards room.

After its days as the morgue, the building housing Captain Tony’s served as everything from a telegraph station to a brothel, and eventually became the first location for Sloppy Joe’s.

But the building still had some dark secrets to reveal…

When you visit Captain Tony’s, you’ll notice a giant tree, typically sporting various amounts of lingerie. Well, that’s the hanging tree.

Yep. A hanging tree.

Legend says 17 pirates met their maker from a rope on this tree in the 1800s, but the pirates aren’t the most notorious people to swing from the hanging tree. The “Lady in Blue,” as she’s commonly referred to, chopped up her husband and two sons in the late 1800s. When found in her blood-stained blue dress, the townspeople took her down to the hanging tree and that was that.

Or so they thought.

These days, she’s the most commonly sighted/mentioned/talked about ghost said to still haunt Captain Tony’s to this day.

As if this all wasn’t dark enough, the bar owners found another creepy surprise in the 1980s when they discovered about a dozen different bodies under the old wooden floorboards.

Even with its haunting past, the property became one of the biggest hotspots in Key West with the opening of Sloppy Joe’s in the 1930s. Famous folks like Ernest Hemingway became regulars, but when a rent increase led the owners to abandon the spot for Duval Street, Hemingway demanded he get the urinal. After all, “I paid for it,” he quipped. These days, that same urinal serves his many cats at the Hemingway House just a few blocks away.

After Sloppy Joe’s relocated, the property operated as the Duval Club before eventually being purchased in 1958 by Anthony Tarracino, the man we know as Captain Tony.

For the next several years, Captain Tony’s became a place known for rowdy fun and excellent live music. It was here where Jimmy Buffett truly mastered his Key West sound. He immortalized Captain Tony in his famous song, “Last Mango in Paris.”

Captain Tony eventually sold the bar in the late 1980s, but his rambunctious spirit lives on even today as the bar gives locals and tourists alike a real Key West experience.

Captain Tony’s own life story is something legends are made of… A checked past, colorful vocabulary, and infamous sex drive didn’t stop him from becoming mayor of Key West for 2 years- two years he described as the greatest of his life. For a fantastic oral history of the bar from Captain Tony himself, check out this interview below...

Captain Tony was a man larger than life, and his life story is a remarkable mix of fact, legend, and fable. For a little more on the Captain, just read his out-of-this-world obituary.

Thanks to Alan's Mysterious World for much of the ghost lore in their original interview posted here.

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