One Of Florida's Oldest And Most Famed Bars Is A Legendary Key West Classic

After spending a day exploring the waters of Key West, there's no better way to cap it off than with a visit to a bar that's as legendary as the island itself. Nestled on Greene Street, Captain Tony's Saloon is more than just a watering hole — it's a vital piece of Key West history and is ranked as one of the four best dive bars in Key West by local resort The Marker.

Originally built in the 1850s as an icehouse and morgue, Captain Tony's has established itself as a beloved gathering place for eccentric locals, rowdy sailors, and adventurous tourists alike. It's where Jimmy Buffett got his start, and he wrote about the bar in the song "Last Mango in Paris." Rumor has it that the ghosts of its former lives still linger, but don't let that scare you off — the spirits here are mostly behind the bar.

Whether you're drawn in by the live music, games of pool, or the quirky charm of dollar bills and bras hanging from the rafters, Captain Tony's Saloon is a Key West classic you won't want to miss. Step inside, order a drink, and get ready to be part of a story that's been unfolding for over a century.

Captain Tony's Saloon endured many transformations before it became the well-known bar it is today. After its first stint as an icehouse and morgue, the building on Greene Street was a telegraph station in the 1890s. As the decades rolled on, it became a cigar factory, then a brothel, before earning its first taste of nightlife infamy as a gay bar in the early 1900s.

In 1933, the space was reborn again, this time as Sloppy Joe's Bar. It quickly became a favorite haunt of Ernest Hemingway, who even took one of the bar's urinals and put it in his house, where visitors can still see it today as a water trough for his cats.

The building found its true identity in 1958 when Captain Tony Tarracino — a former boat captain, gunrunner, and at one point the mayor of Key West — purchased it. Today, the bar stands proudly just a short walk from the artsy plaza of Mallory Square. Though Captain Tony sold the bar when he became mayor, he's still enshrined as a part of the bar's history, both in its namesake and in the Atlantic goliath grouper hanging above the door, which Captain Tony caught himself and preserved.

If you're doing ghost tours across America, Captain Tony's Saloon fits right into the journey. While the bar may be known for its lively atmosphere, it's also home to a few spectral guests who are never too far from the action. Perhaps the most morbid feature of the bar is the infamous "Hanging Tree" standing in the middle of the bar, on which, according to a local hotel called Old Town Manor, 18 people were supposedly hanged. 

All but one of those 18, the story goes, were pirates. The outlier was a woman now known as the "Lady in Blue," who is ranked as one of Key West's most infamous ghosts by ghost tour company Ghosts & Gravestones. Legend has it that she murdered her husband and two sons. When she was hanged, she was wearing a blue dress, and you may recognize her ghost by seeing a bluish glow.

If that wasn't enough, there are also two graves within the bar itself. Look for two gravestones marked with the names Elvira and Reba Sawyer. Elvira was supposedly hanged on the Hanging Tree for killing her husband. The story behind Reba's grave is that she had an affair at the bar. After she died, her husband found out she was having the affair and moved her grave to the place where she cheated on him. But no matter how spooky the stories, the atmosphere of Captain Tony's remains vibrant and welcoming. After all, where else can you enjoy a cold drink while sharing a laugh with both the living and the dearly departed?