Key West Attractions – Sloppy Joes Bar
Sloppy Joe’s Key West: Where Island History Meets Legendary Good Times
If you’ve ever walked down Duval Street in Key West, chances are you’ve heard the music before you saw the sign. That lively sound almost always leads to one place: Sloppy Joe’s Bar — a true Key West landmark and one of the most famous watering holes in Florida. More than just a bar, Sloppy Joe’s is part of the island’s soul.
A Bar with Deep Roots in Key West History
Sloppy Joe’s opened in 1933, right after Prohibition ended, making it one of the oldest continuously operating bars in Key West. It quickly became a favorite hangout for locals, fishermen, travelers, and writers — including Ernest Hemingway, who lived just a few blocks away. Legend has it that the bar got its name during a rush to move liquor from one location to another before authorities arrived. Bottles were passed hand to hand, things got messy, and someone reportedly joked about the operation being “sloppy.” The name stuck. Since then, Sloppy Joe’s has been serving drinks, food, and entertainment for nearly a century.
The Heart of Duval Street
Located right in the middle of Duval Street, Sloppy Joe’s is impossible to miss. Open-air seating spills onto the sidewalk, live music fills the air, and crowds flow in and out from morning to late night. It’s the kind of place where: Tourists mingle with locals, Flip-flops are always acceptable attire, Frozen drinks appear faster than sunsets, every night feels like a celebration, whether you stop in for one drink or stay for hours, Sloppy Joe’s delivers classic Key West energy — relaxed, loud, friendly, and unforgettable.
Famous Drinks and Casual Island Eats
Sloppy Joe’s is known for its oversized drinks and casual comfort food. Their menu features island favorites like burgers, wings, conch fritters, seafood baskets, and, of course, their famous Sloppy Joe sandwich. Pair your meal with one of their popular cocktails or frozen drinks, and you’ve got the full experience. It’s not fancy dining — it’s fun dining, the kind that fits perfectly with salty air and live music.
Live Music Every Day
One of the biggest draws at Sloppy Joe’s is the music. Bands play throughout the day and night, covering everything from classic rock to island tunes. The dance floor fills quickly, and it’s not unusual to see strangers singing together by the end of the night. Music is part of the bar’s identity — it keeps the energy high and the vibe unmistakably Key West.
More Than a Bar: A Key West Tradition
Over the years, Sloppy Joe’s has become more than a place to grab a drink. It’s hosted fishing tournaments, festivals, and countless celebrations. Visitors return year after year, and first timers often make it a must-stop destination. For many, a trip to Key West simply isn’t complete without stepping inside Sloppy Joe’s.
Why Sloppy Joe’s Still Matters
What makes Sloppy Joe’s special isn’t just its history — it’s its ability to stay true to the spirit of Key West. It’s casual, welcoming, and full of life. No reservations required. No dress code. Just good music, cold drinks, and stories waiting to happen. Sloppy Joe’s represents everything people love about the island: freedom, fun, and a sense that time slows down just a little when you’re here.
