A tree grows straight through the middle of this bar and pokes out the roof.
Legend calls it the old Hanging Tree, and the saloon has kept those spooky stories close for decades.
There’s also a gravestone under the barroom floor.
Workers found it during 1980s renovations, along with bones from more than a dozen people.
I like how this Florida landmark refuses to tidy up its past.
Stools carry painted names like Ernest Hemingway, Jimmy Buffett, and Truman Capote.
Bras dangle from the rafters, and business cards crowd the weathered walls.
I can’t imagine a stranger or friendlier spot to rest your feet on a sunny island afternoon.
A live band plays nightly, and a giant fish hangs over the front door waiting for your lucky quarter.
So which famous stool will you claim first?
A Building Older Than Most Of America’s Bar Stories
Captain Tony’s Saloon sits inside a building dating back to 1851 or 1852. That’s older than plenty of towns, and it shows in every weathered board.
The first known job here was an icehouse. It also served as the city morgue, which explains a few of the chilly stories you’ll hear later.
By the 1890s, the building held a wireless telegraph station. News of the battleship Maine’s sinking in 1898 passed through here, which is pretty wild for a spot now known for music.
The list of past lives keeps going. Records point to a cigar factory in 1912, a bordello, and a hangout for Navy sailors.
Several speakeasies operated here too. One carried the memorable nickname The Blind Pig, which sounds like a mystery novel waiting to happen.
In 1962, David Wolkowsky took over the building, which became known as The Oldest Bar. That name stuck in spirit, and Florida still points to this address with that title today.
Knowing this backstory changes how the room feels. Every corner has stacked up more than a century of reinventions, and it still opens its doors each morning.
Meet The Wild Captain Who Gave The Place Its Name
Anthony Tarracino had one of the busiest résumés in Key West history. He worked as a charter boat captain, gambler, and gunrunner before buying this bar.
He purchased it from David Wolkowsky in 1968. Then he renamed it Captain Tony’s Saloon, and his nickname became part of island legend.
The story gets better. From 1989 to 1991, Captain Tony served as Mayor of Key West, which is a fun twist for a saloon owner.
Later, the city gave him the title Mayor Emeritus. Few bar owners can say their business card included city hall.
His legacy lives on in the room. Historic photos and memorabilia fill the walls, so you can spot bits of his colorful life while the band warms up.
The saloon still honors him every year. Captain Tony Day lands on August 10th, so mark your calendar if your trip falls in mid-August.
I believe that’s the secret to the bar’s lasting charm. It isn’t built around a theme someone dreamed up.
It’s built around a real person who lived big, and the walls still remember him.
That Tree In The Middle Of The Room Has Stories To Tell
Most bars put a pillar in the center of the room. This one has a full tree, and it grows right up through the roof.
Local legend says it was Key West’s old Hanging Tree. According to those tales, 17 people met their end there, including several pirates.
The saloon leans into that reputation. Still, the details mix real history with a healthy dose of folklore, so treat it like a campfire story.
Either way, the tree makes a memorable centerpiece. You can stand beside a trunk that has watched this island change for a very long time.
Look closely at what hangs around it. Bras and other odd decorations drift down from the rafters, which adds a goofy contrast to the eerie legend.
It’s a great spot for photos, too. Few places let you pose next to a living tree indoors while live music plays a few feet away.
Kids of all ages love a good spooky tale. Grown-ups do too, and this one comes with a real trunk you can actually see and touch.
Watch Your Step Near The Gravestone Under The Floor
Renovations usually turn up old pipes or forgotten coins. In the 1980s, workers here found the bones of somewhere between 15 and 18 people.
They also uncovered a gravestone. A gravestone belonging to a young woman named Elvira Drew was discovered during renovations in the 1980s, and her grave marker is now displayed beside the pool table.
That detail gives Captain Tony’s Saloon a mood you won’t find at a shiny new spot. Remember, the building once served as the city morgue, so the pieces start to fit together.
Visitors can still find the marker. It’s a quiet, thoughtful corner inside an otherwise lively room.
Take a moment there before heading back to the music. It’s a good reminder that real people walked this island long before the souvenir shops arrived.
History buffs will want to snap a picture. Ghost-story fans will want to tell everyone back home.
A tip for families: give younger visitors a heads-up first. The marker is more fascinating than frightening, but a little warning helps everyone enjoy it.
Few bars offer this kind of conversation starter. Fewer still have one right under your feet.
Grab A Seat Once Claimed By Legends
Ernest Hemingway, Truman Capote, and Harry Truman all have something in common here. Their names are painted on barstools you can actually sit on.
The lineup keeps rolling with Jimmy Buffett, Shel Silverstein, and John Prine. Bob Dylan, John F.
Kennedy, and football coach Mike Leach make the list too.
Hemingway’s link runs deep. From 1933 until about 1938, this building was the original Sloppy Joe’s Bar, owned by Josie Russell, and Hemingway was a regular.
A rent increase sent Sloppy Joe’s over to Duval Street in 1938. The building stayed put, though, and so did the stories.
Picking a stool becomes its own little game. Do you go with a president, a poet, or a songwriter who wrote about cheeseburgers?
Shel Silverstein fans might feel a special thrill. Sitting where the author of kids’ favorite poems once sat is a sweet bonus.
Go early if you have a favorite name in mind. A popular stool can get claimed fast, and nobody wants to arm-wrestle a stranger over Truman Capote.
Live Music Fills The Air From Afternoon To Late Night
Jimmy Buffett started his Key West career right here in the early 1970s. The story goes that he often got paid in tequila instead of cash.
He later gave the bar a shout-out in his song Last Mango in Paris. Captain Tony shows up in that tune too, so fans should cue it up before visiting.
Music still sits at the heart of Captain Tony’s Saloon. Live entertainment runs every afternoon, and a band takes the stage every night.
That makes timing easy. Show up after lunch for a mellow set, or swing by after sunset when the night picks up speed.
The hours help, too. Doors open at 10 AM most days and 10:30 AM on Sunday, with closing at 2 AM, or 1 AM on Sunday.
I like that a place with so much history still feels alive. Old photos hang on the walls while new songs bounce off them.
Who knows? The musician strumming tonight might be the next big name painted on a stool someday.
Toss A Quarter At The Giant Fish For Island Luck
Look up before heading inside. A preserved Atlantic goliath grouper hangs above the sign, and Captain Tony caught it himself.
Goliath groupers are massive fish, so this one makes quite a doorman. It’s probably the only bouncer in town that never blinks.
A fun tradition comes with it. Toss a quarter into the fish’s mouth, and you’ll supposedly have good luck until you leave the island.
Easier said than done. That mouth sits high above the door, so expect plenty of misses and plenty of laughs.
Here’s a tip: bring a handful of quarters. Your first throw might bounce off the sign, and your second might land somewhere surprising.
It’s a great family moment, too. Anyone can join in, and the bragging rights last the whole vacation.
The fish ties right back to the captain’s charter boat days. It’s a little piece of his ocean life, hanging in plain view on a busy Key West street.
Land one in and you’ll want a photo. Miss them all, and you’ll still have a good story.
Walls Covered In Cards, Photos, And Pure Island Weirdness
Nobody would call the decor minimalist. Countless business cards cover the weathered walls, and bras hang from the rafters like quirky party streamers.
Historic photographs and memorabilia fill in the gaps. Your eyes will bounce around the room for a good while.
Captain Tony’s Saloon wears the dive bar label proudly. It’s a casual Old Town gathering spot, and it doesn’t pretend to be anything fancy.
Pool tables give you something to do between songs. Rack up a game with friends while the band plays on.
Hunting for odd details turns into a fun challenge. Try spotting the oldest photo or the funniest card you can find.
If you own a business, consider bringing a card along. Adding your own to the collection is a sneaky way to become part of the place.
The room feels like a scrapbook made by thousands of strangers. Each layer tells you someone stopped by, laughed, and left a little piece behind.
That messy, friendly chaos is exactly the point. Polished bars are everywhere, but this kind of personality takes decades to grow.
Easy To Find, Hard To Leave Without A Souvenir
Finding the place takes no treasure map. You’ll find it at 428 Greene St, Key West, FL 33040, right in Old Town.
That location puts you close to the island’s busiest strolling streets. Sloppy Joe’s newer Duval Street home is nearby, so you can compare both chapters of the same story.
Before leaving, check out the merchandise. Captain Tony’s Saloon sells t-shirts, long-sleeve shirts, visors, and bottle coolies.
A visor might be the smartest buy. The Florida sun doesn’t take days off, and shade on your face helps on a long walk.
A shirt also makes an easy gift. Friends back home get a piece of the oldest bar story without the trip.
The saloon serves a house specialty called Pirate’s Punch, too. It fits the pirate legends swirling around the tree inside.
Plan for a visit that’s longer than you expect. Between the stools, the grave marker, the music, and that stubborn fish, an hour disappears fast.
And honestly, that’s the best kind of problem. Some spots you check off a list, but this one invites you to stay a while.
