The Florida Saloon Supposedly Built Around An Old Pirate-Hanging Tree

Legend has it there's a huge ficus tree with a morbid history growing in the middle of one of Florida's oldest bars. They say it was a hanging tree, where criminals and pirates were executed in the 1800s. You can ask the bartender to make you a Pirate Punch, the bar's signature rum cocktail, while you sit next to the trunk under a canopy of dollar bills and women's bras — they're stapled to the ceiling; the tree's branches grow out of the top of the building. Perhaps you'll be joined by the ghosts of those whose lives supposedly ended in that very spot. If you join one of the ghost tours going through the bar, you'll certainly hear chilling stories about the place.

Pirate executions are just part of the lore of Captain Tony's Saloon on Greene Street. Housed in a yellow wooden building with an open-mouthed fish above the door, it was originally built in the mid-1800s as an ice house that doubled as the city morgue. Later, it was converted into a telegraph station and became a bar several times over, drawing in famous customers, including Jimmy Buffett (his favorite drink wasn't actually a margarita, by the way) and Ernest Hemingway.

Through the years, the lore of the "Hanging Tree" has haunted the building, drawing in customers and contributing to an overall pirate-style vibe. But the supposed 1820s incident isn't documented. It's a story, passed down through generations of island-dwellers and bartenders — one that can't quite be confirmed by history.

Captain Tony's expanded at the beginning of the 20^th century to encompass the "Hanging Tree" inside the building. If you read the saloon's website, you could be convinced the tree's deadly history is true. But, nobody wrote down an account that confirms 16 pirates and a woman convicted of killing her husband and children were hanged from that specific tree. And some sources say more than 75 people were executed at that tree, so the numbers vary drastically. However, there are some documented facts relating to the pirate era that could confirm the story is at least possibly true.

Key West is rich with pirate history because the shallow waters around the islands were perfect havens and hiding spots for their ships. Pirates were prolific enough to become targets of a U.S. government-ordained anti-piracy squadron in 1822. After the pirate hunters sailed into the islands, pillaging ships were chased off to less-patrolled waters. Pirates who were caught were often hanged for their crimes, so the story of the hanging tree at Captain Tony's fits the general profile for the neighborhood at the time. But, there are accounts of captured pirates avoiding execution entirely and being imprisoned, instead. As it is with most pirate lore, we may never know the truth of the "Hanging Tree," but what is certain is that it provides a chilling adventure when you've had your fill of everything Key West has to offer — including some of the best Cuban sandwiches in the USA.