- Attraction: Captain Tony’s Saloon
- Location: 428 Greene Street, Key West, FL 33040
- Industry: Bar
- Website: https://capttonyssaloon.com/
Picture walking into a bar where Ernest Hemingway once nursed his drinks, where Jimmy Buffett played for tequila payments, and where a massive tree grows straight through the middle of the room—a tree that once served as the town’s hanging gallows.
This surreal scene awaits you at Captain Tony’s Saloon, Florida’s oldest bar and perhaps Key West’s most fascinating piece of living history.
The weathered building at 428 Greene Street has witnessed more drama than a Hemingway novel. Built in 1851 as an ice house and city morgue, this structure has been everything from a telegraph station that reported the sinking of the USS Maine to a speakeasy, bordello, and cigar factory.
But it’s most famous for housing the original Sloppy Joe’s Bar from 1933-1938, where Hemingway spent his evenings crafting stories and nursing drinks. When the rent went up by just one dollar per week in 1938, the entire bar literally packed up and moved across the street—customers, barstools, and all.
Historic Highlights & Famous Connections
The Hanging Tree: The massive tree growing through the center of the bar once stood outside as Key West’s execution site. Seventeen people met their end here, including sixteen pirates and one woman who was hanged for killing her abusive husband and children. You can still see the gnarled branches reaching through the roof, creating an eerie centerpiece that’s both beautiful and haunting.
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Keep Exploring →Celebrity Barstool Collection: Every seat tells a story here. You’ll find barstools painted with the names of famous patrons like Ernest Hemingway, Truman Capote, Jimmy Buffett, John F. Kennedy, Harry Truman, and Shel Silverstein. Each stool represents someone who not only visited but regularly frequented this legendary watering hole.
Jimmy Buffett’s Origins: This is where the Parrothead phenomenon began. In the early 1970s, a young Jimmy Buffett played acoustic sets here, often paid in tequila rather than cash. He immortalized both the bar and its colorful owner in his song, cementing Captain Tony’s place in music history.
The Lucky Grouper: Above the entrance hangs a massive Atlantic goliath grouper that Captain Tony himself caught. Local legend says if you can toss a quarter into the fish’s mouth, good luck will follow you for the rest of your Key West visit.
Pirate Punch & Captain Tony’s Amber: The signature drinks here have become classics. The Pirate Punch delivers a fruity tropical punch with a serious kick, while Captain Tony’s Amber Ale offers a smooth, locally-brewed flavor that even non-beer drinkers appreciate.
Atmosphere & Unique Décor
Authentic Dive Bar Character: You’ll step into perpetual twilight here—the interior stays deliberately dim and moody, creating that authentic dive bar atmosphere that feels frozen in time. It’s the kind of place where sunlight seems to stop at the door, leaving you in a world of shadows and stories.
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Discover MoreCeiling of Memories: Look up and you’ll be amazed by the thousands of dollar bills, business cards, and women’s bras covering every inch of the ceiling. This eclectic collection represents decades of visitors leaving their mark, creating a living museum of memories and mementos.
Gravestone Discoveries: During renovations in the 1980s, workers discovered skeletal remains and gravestones under the floorboards, including one for a young woman named Elvira. Her marker now sits permanently by the pool table, adding to the bar’s macabre charm.
Original Historic Elements: The walls are plastered with license plates, vintage signs, and decades of accumulated memorabilia. Pool tables occupy the back room where gambling once thrived, and every surface tells part of Key West’s wild history.
Other Considerations
Reasonable Pricing: You’ll find Captain Tony’s offers fair dive bar pricing that won’t break your vacation budget. Most drinks fall into the affordable range, though you might pay a slight premium for the historical significance and tourist appeal.
Live Music Tradition: The musical legacy continues with live performers every afternoon and evening. You’ll experience everything from classic rock acoustic sets to island-style tunes, maintaining the tradition that launched Jimmy Buffett’s career.
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Keep Exploring →Easy Downtown Access: Located just off busy Duval Street on Greene Street, you’ll find Captain Tony’s perfectly positioned for bar hopping. The location offers easier parking than Duval Street establishments while remaining within walking distance of everything.
Family-Friendly During Day: Despite its adult reputation, you’ll discover the saloon welcomes families during daytime hours. The historical significance makes it educational, though the atmosphere becomes more adult-oriented as evening approaches.
Ghost Stories & Paranormal Activity: You might experience more than just history here. Many visitors report unexplained phenomena, particularly around the women’s restroom and near the hanging tree. Whether you believe in spirits or not, the atmosphere certainly feels otherworldly.
Best Visiting Times: You’ll enjoy the most authentic experience during late afternoon or early evening when live music starts but before the heavy tourist crowds arrive. This sweet spot gives you time to absorb the history while still catching the entertainment.
Captain Tony’s Saloon
📍 428 Greene Street, Key West, FL 33040
