Few places are as closely connected to Key West history and nightlife as Sloppy Joe’s Bar. Located at the corner of Duval and Greene streets, this legendary saloon combines live music, casual food, cold drinks, colorful history, and the unmistakable energy of Old Town.
Sloppy Joe’s history began in 1933, immediately after the end of Prohibition. The bar moved to its current Duval Street location in 1937 and has since become one of Key West’s most recognizable landmarks.
A Key West Landmark Since 1933
Sloppy Joe’s opened on December 5, 1933, just one day after Prohibition ended. The original establishment operated nearby before moving to its current location at the corner of Duval and Greene streets.
Over the decades, the bar has welcomed generations of residents, travelers, writers, musicians, and island characters. Today, Sloppy Joe’s is listed on the National Register of Historic Places and remains one of the most famous bars in the country.
Courtesy of KeyTV
The Hemingway Connection
Sloppy Joe’s is closely associated with author Ernest Hemingway, who lived in Key West during the 1930s and became a regular patron of the original establishment.
Stories of Hemingway sharing drinks and conversation with friends helped establish the bar’s place in Key West folklore. Historic photographs, memorabilia, and the annual Hemingway Look-Alike Contest continue to celebrate that connection.
The contest is held each July and draws bearded competitors and Hemingway fans from around the world.
Live Music Every Day
Live entertainment is a major part of the Sloppy Joe’s experience. Bands and performers take the stage throughout the day and into the night, with music offered every day of the year.
Depending on the schedule, visitors may hear:
- Rock and classic rock
- Country
- Blues
- Island music
- Acoustic performers
- Local and touring bands
Dancing begins each evening, and the official entertainment calendar lists the performers scheduled to appear.
Food, Drinks and Key West Favorites
Sloppy Joe’s serves casual American and Key West-inspired food alongside frozen cocktails, beer, wine, and specialty drinks.
Menu selections may include:
- The signature Sloppy Joe sandwich
- Wings and appetizers
- Burgers
- Sandwiches and wraps
- Pizza
- Key West snacks
- Salads
- Tropical cocktails
- Frozen drinks
- Beer and wine
The atmosphere is relaxed and lively, making it a convenient choice for lunch, dinner, drinks, or a break while exploring Duval Street.
Webcams, Shopping and Special Events
Sloppy Joe’s offers several live webcams showing the stage, bar, crowd, and activity along Duval Street. Visitors can check the atmosphere before arriving or revisit the Key West experience after returning home.
The property also includes a retail store featuring branded clothing, hats, souvenirs, and gifts.
Special events take place throughout the year, with the annual Hemingway Look-Alike Contest remaining one of the most famous.
Close to Key West Express and Old Town Attractions
Sloppy Joe’s is approximately 0.5 miles from the Key West Express terminal, making it about a 10-minute walk through the Historic Seaport and Old Town.
Nearby attractions include:
- Duval Street
- Mallory Square
- Key West Historic Seaport
- Key West Aquarium
- Mel Fisher Maritime Museum
- Key West Museum of Art & History at the Custom House
- Captain Tony’s Saloon
- Hog’s Breath Saloon
Its central location makes Sloppy Joe’s an easy stop at almost any point during a day in Key West.
Frequently Asked Questions
Where is Sloppy Joe’s located?
Sloppy Joe’s is located at 201 Duval Street, at the corner of Duval and Greene streets in Old Town Key West.
How far is Sloppy Joe’s from the Key West Express terminal?
Sloppy Joe’s is approximately 0.5 miles from the terminal, or about a 10-minute walk.
When did Sloppy Joe’s open?
Sloppy Joe’s opened on December 5, 1933, one day after Prohibition ended. It moved to its current location in 1937.
Why is Sloppy Joe’s famous?
The bar is known for its Key West history, connection to Ernest Hemingway, daily live music, annual Hemingway Look-Alike Contest, and lively Duval Street atmosphere.
Does Sloppy Joe’s have live music?
Yes. Sloppy Joe’s features live entertainment every day, with performers appearing throughout the day and evening.
Does Sloppy Joe’s serve food?
Yes. The menu includes the signature Sloppy Joe sandwich, wings, burgers, sandwiches, pizza, appetizers, and other casual favorites.
Is Sloppy Joe’s family-friendly?
Families often visit for lunch or during the daytime. The atmosphere becomes louder and more adult-oriented as the evening entertainment begins.
Does Sloppy Joe’s have a gift shop?
Yes. The retail store sells branded clothing, hats, souvenirs, gift cards, and other Sloppy Joe’s merchandise.
Experience a Key West Original
From its Hemingway history and daily live music to its casual food and energetic Duval Street setting, Sloppy Joe’s Bar remains an essential Key West experience.
Travel aboard Key West Express, arrive near the Historic Seaport, and enjoy an easy walk to one of the island’s most famous gathering places.
