Few places capture Key West’s colorful history quite like Captain Tony’s Saloon. Located just off Duval Street in Old Town, this legendary watering hole has welcomed writers, musicians, locals, and curious visitors for generations.
The building dates to 1851 and originally served as an icehouse that also doubled as a morgue. Today, its weathered walls, unusual decorations, live music, and larger-than-life stories make Captain Tony’s one of the most memorable bars in Key West.
A Building Filled with Key West History
Long before Captain Tony’s became a saloon, the building at 428 Greene Street served several purposes throughout Key West’s history.
Its earliest known use was as an icehouse, which provided one of the few cool places on the island during the mid-1800s. Because refrigeration was unavailable, the building was also reportedly used as a morgue.
Over the years, the property has housed a variety of businesses and gathering places, each adding another chapter to its colorful past.
The Famous Hanging Tree
One of the most unusual features inside Captain Tony’s is the large tree growing through the center of the building and out through the roof.
Local legend identifies it as Key West’s former Hanging Tree, where 17 people were reportedly executed, including several pirates. The saloon embraces these stories as part of its haunted reputation, although many details have become a mixture of documented history, folklore, and island legend.
Visitors often photograph the tree and look for the grave marker located beneath the barroom floor.
A Favorite of Writers, Musicians, and Key West Characters
Captain Tony’s has long been associated with some of Key West’s most recognizable personalities.
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Photo Credit: CedarBendDrive from USA, CC BY 2.0, via Wikimedia Commons
The saloon’s official history connects the establishment with:
- Ernest Hemingway
- Truman Capote
- Tennessee Williams
- Shel Silverstein
- Jimmy Buffett
Jimmy Buffett performed at Captain Tony’s during the early years of his career and later referenced the saloon and its colorful owner in his music. The stories surrounding these famous visitors have helped make Captain Tony’s an essential stop for fans of Key West history and culture.
The Life of Captain Tony Tarracino
The saloon was named for Anthony “Captain Tony” Tarracino, one of Key West’s most unforgettable residents.
During his remarkable life, Captain Tony worked as a charter boat captain, gambler, gunrunner, saloon owner, and local politician. He served as mayor of Key West from 1989 to 1991 and was later honored with the title of Mayor Emeritus.
Known for his storytelling, adventurous personality, and love of Key West, Captain Tony became nearly as legendary as the saloon that bears his name.
Live Music and Classic Island Atmosphere
Captain Tony’s remains a casual Old Town gathering place where visitors can enjoy cold drinks, live entertainment, and a setting unlike any other bar in Key West.
Guests stop in for:
- Live music
- Cold beer and cocktails
- The signature Pirate’s Punch
- Historic photographs and memorabilia
- Colorful local stories
- Captain Tony’s merchandise
- An unmistakably Key West atmosphere
The interior is covered with business cards, license plates, signed memorabilia, currency, and other items left behind by visitors over the years.
Easy to Reach from Key West Express
Captain Tony’s Saloon is approximately 0.6 miles from the Key West Express terminal, making it roughly a 12-minute walk through the Historic Seaport and Old Town.
Nearby attractions include:
- Duval Street
- Mallory Square
- Key West Historic Seaport
- Sloppy Joe’s Bar
- Hog’s Breath Saloon
- Mel Fisher Maritime Museum
- Key West Aquarium
- Key West Museum of Art & History at the Custom House
Its central location makes Captain Tony’s an easy stop while exploring many of Key West’s most popular attractions.
Frequently Asked Questions
Where is Captain Tony’s Saloon located?
Captain Tony’s Saloon is located at 428 Greene Street in Old Town Key West, just steps from Duval Street.
How far is Captain Tony’s from the Key West Express terminal?
The saloon is approximately 0.6 miles from the terminal, or about a 12-minute walk.
Why is Captain Tony’s Saloon famous?
Captain Tony’s is known for its historic 1851 building, colorful former owner, famous visitors, live music, unusual decorations, and legendary Hanging Tree.
Is Captain Tony’s Saloon haunted?
Captain Tony’s is frequently described as one of Key West’s haunted locations. Stories involve the building’s former use as a morgue, the Hanging Tree, and unexplained experiences reported by visitors and employees.
Did Jimmy Buffett perform at Captain Tony’s?
Yes. Jimmy Buffett performed at Captain Tony’s early in his career and had a personal connection with Captain Tony Tarracino.
Does Captain Tony’s have live music?
Yes. The saloon regularly features live entertainment, although performers and schedules can change.
Does Captain Tony’s serve food?
No. Captain Tony’s is primarily known as a bar and live-music venue rather than a full-service restaurant. But, you can get some bites from neighboring spots and bring it inside.
Is Captain Tony’s family-friendly?
The saloon may be suitable for families earlier in the day, but the atmosphere becomes more adult-oriented as the evening progresses.
Experience a Key West Legend
From its historic building and haunted legends to its famous visitors and live island music, Captain Tony’s Saloon offers a glimpse into the unconventional spirit that makes Key West so unique.
Travel aboard Key West Express, arrive near the Historic Seaport, and take an easy walk through Old Town to one of the island’s most legendary watering holes.
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