This Key West Saloon Has Been Around For 80+ Years With A Bizarre Atmosphere

Captain Tony’s Saloon in Key West isn’t just a place to grab a drink—it’s a time capsule.

For over 80 years, this legendary watering hole has hosted pirates, poets, presidents, and plenty of rowdy adventurers. But what keeps visitors coming back isn’t just the booze.

It’s the bras on the ceiling, the haunted tree in the middle of the room, and the feeling that Hemingway himself might sidle up to the bar beside you.

Captain Tony’s Saloon wears its past like a badge of honor. Originally built as a morgue in 1851, the building later became a cigar factory, icehouse, and even a telegraph station before morphing into the bar we know today.

But forget stuffy exhibits. Here, history is alive—and weird.

Dollar bills and bras dangle from the ceiling, left behind by decades of visitors.

License plates and business cards plaster the walls, creating a mosaic of global wanderers.

Hardwood floors creak underfoot, groaning with the weight of countless secrets.

The bar’s namesake, Captain Tony Tarracino, was a larger-than-life figure: a gambler, smuggler, and Key West mayor. His spirit—along with a few others—is said to linger in every corner.

The Hanging Tree: Where Macabre Meets Margaritas

Yes, there’s a tree growing inside the bar.

But this isn’t just any tree.

The massive gnarled trunk in the center of the room is the infamous “Hanging Tree.”

In the 1800s, it served as a gallows for 17 people when the building was a courthouse. Today, its branches hold trinkets, photos, and Christmas lights—a quirky juxtaposition of grim history and island cheer.

“It’s like Mother Nature decided to crash the party and never left,” joked one local.

Captain Tony’s has also been known to attract rebels and legends.

Ernest Hemingway drank here while penning To Have and Have Not.

Jimmy Buffett immortalized it in his song Last Mango in Paris.

Even JFK and Harry Truman reportedly stopped by.

But the bar’s true stars are its “regulars” from beyond the grave. Staff and visitors swear the saloon is haunted.

“You don’t just visit Captain Tony’s—you join its story,” said a bartender.

Drinks and Flair

The cocktails here aren’t just poured—they’re performed.

Bartenders double as storytellers, mixing rum runners with tales of shipwrecks and bar brawls.

Here are a few must-try drinks to sip on if you visit:

Pirate’s Punch: A fruity, rum-heavy concoction that’s stronger than it tastes.

Captain Tony’s Amber Ale: A smooth, malty beer brewed locally.

“The Hemingway”: A stiff whiskey order, unofficially named for the writer’s favorite order.

Tip: Watch your pour size. Some visitors report getting short-changed in souvenir cups. Stick to bottled beer or clarify your order to avoid surprises.

By day, Captain Tony’s feels like a sleepy relic. By night, it transforms into a raucous pirate ship. Local musicians belt out blues, rock, and Buffett covers, while crowds sing along.

“The music wraps around you like the humidity here—you can’t escape it, and you don’t want to,” said a recent visitor.

Grab a stool near the guitarists, and you might hear a Shel Silverstein poem set to music or a Dylan cover with a Keys twist.

Visitor Sentiments

Captain Tony’s polarizes people. Its grit is part of the charm—or the turnoff.

The Good:

• “Best dive bar in town! The history gives you chills.”
• “Strong drinks, cold beer, and Gabriel Wright’s live music = perfection.”
• “Smoking allowed! Feels like stepping into old Florida.”

The Bad:

• “Bartenders can be gruff—don’t expect smiles.”
• “Touristy crowds get loud.”
• “Skip the draft beer; go for bottles.”

Or perhaps my favorite take that I think encapsulates this place:

“It’s a mess… and I loved every second.”

Ready to Raise a Glass?

In a world of sanitized, Instagram-ready bars, Captain Tony’s is gloriously unpolished.

It’s a reminder of Key West’s wild past—a place where outcasts and artists carved out a life between the ocean and the chaos.

You won’t find fancy cocktails or velvet ropes. But you’ll find sticky floors, cold beer, and the sense that you’re part of something bigger.

You might walk in as a stranger, but you could walk out as a legend.

Captain Tony’s Saloon
📍428 Greene St, Key West, FL 33040