Few establishments are as closely tied to Key West as Sloppy Joe’s Bar. Its bright corner entrance, live music and connection to Ernest Hemingway have made it one of the most recognizable stops on Duval Street.
Yet Sloppy Joe’s is more than a famous place to order a drink. Its history reaches back to the end of Prohibition, when Key West’s waterfront culture brought together fishermen, writers, rum runners and independent personalities. Today, the bar remains a lively gathering place where visitors can experience a piece of that history while enjoying food, music and the energy of Old Town.
Whether you are visiting for the first time or returning to Key West, here is what to know about the story and experience of Sloppy Joe’s.
Photo Credit: Sloppy Joe's Key West
According to the official history of Sloppy Joe’s Bar, the establishment traces its legitimate beginning to December 5, 1933—the day Prohibition was repealed in the United States.
Owner Joe Russell was a Key West native, fisherman, rum runner and speakeasy operator. After Prohibition, he opened a legal saloon in a modest building at 428 Greene Street. The place was first called the Blind Pig and later became the Silver Slipper after a dance floor was added.
It was never designed as an elegant cocktail lounge. The early establishment had a casual, come-as-you-are atmosphere with inexpensive drinks, pool tables, gambling and a loyal group of local customers. That unpolished character helped turn it into a natural gathering place for the personalities who shaped Key West during the 1930s.
The name is generally associated with a Havana bar that Joe Russell and Ernest Hemingway knew during their time in Cuba. At Hemingway’s encouragement, Russell adopted the Sloppy Joe’s name for his Key West establishment.
The name suited the bar’s informal personality. What began as a modest local saloon eventually became one of the best-known names in Key West hospitality.
Ernest Hemingway lived in Key West through much of the 1930s and became a friend, customer and fishing companion of Joe Russell. Their friendship helped establish the bar’s lasting association with the author.
Hemingway was drawn to the island’s fishing, people and unconventional culture. Sloppy Joe’s offered all three in abundance. Stories of the writer spending time with Russell and other local characters became part of Key West folklore, while photographs and memorabilia helped carry that connection into the present day.
Travelers interested in Hemingway can pair a stop at the bar with the Ernest Hemingway Home & Museum, where he lived and wrote during his Key West years.
Sloppy Joe’s moved from Greene Street to its current home at 201 Duval Street in 1937. The relocation became a Key West story in its own right.
When the lease at the original building ended, Russell enlisted customers to carry the bar’s furniture and fixtures down the street to the new location. Patrons reportedly took their drinks with them, allowing the party to continue during the move.
The original Greene Street building later became Captain Tony’s Saloon. Although the two establishments have separate identities today, visiting both offers an entertaining way to follow the early geography of Sloppy Joe’s through Old Town.
Modern Sloppy Joe’s combines a historic Duval Street setting with the atmosphere of a busy entertainment venue. It is known for live music, casual food, drinks, dancing, special events and a retail shop.
Visitors come for different reasons:
The experience changes throughout the day. Daytime is generally better for travelers interested in lunch, history or a more casual visit. The atmosphere becomes livelier as evening entertainment and nightlife build. Check the official Sloppy Joe’s entertainment calendar before your visit because performers and schedules change.
Sloppy Joe’s serves casual American and Key West-inspired food alongside frozen drinks, cocktails, beer and wine. Menu selections can change, but visitors may find the signature Sloppy Joe sandwich, appetizers, wings, burgers, sandwiches, pizza and other bar favorites.
Live entertainment is central to the experience. The official venue promotes music every day of the year, with local and touring performers appearing onstage. If a particular performer or type of music matters to you, review the current schedule rather than relying on an older itinerary.
Each July, Sloppy Joe’s hosts its annual Hemingway Look-Alike Contest. White-bearded competitors gather to resemble the author in his later years, drawing Hemingway enthusiasts and spectators from around the world.
The contest has become one of the best-known traditions associated with Hemingway Days in Key West. If you hope to attend, plan well ahead: July accommodations, transportation and popular activities can fill as the event approaches. Verify the current contest dates and rules directly with Sloppy Joe’s.
Sloppy Joe’s is located at 201 Duval Street, at the corner of Duval and Greene streets in Old Town Key West.
The bar is approximately half a mile from the Key West Express terminal, making it an easy walk through the Historic Seaport and Old Town. It is also close to Mallory Square, the Key West Aquarium, the Custom House Museum and many restaurants, shops and waterfront attractions.
Use the Key West walking tour guide to connect Sloppy Joe’s with other Old Town landmarks, or explore the complete guide to Duval Street when planning a longer route.
Photo Credit: Sloppy Joe's Key West
Photo Credit: DeWolfe and Wood Collection in the Otto Hirzel scrapbook - Photo Florida Keys Public Library collection., Public Domain
Key West Express provides passenger ferry service between Fort Myers Beach and Key West aboard jet-powered catamarans. The Key West terminal is near the Historic Seaport, placing Sloppy Joe’s and many other Old Town attractions within easy reach after arrival.
Before traveling, review the current Key West Express fares and sailing schedule. Boarding requirements and available travel dates can change, so build your Key West plans around the sailing information for your specific trip.
Book your Key West Express trip and experience the history, music and colorful personality of Sloppy Joe’s and Old Town Key West.
Sloppy Joe’s is located at 201 Duval Street, at the corner of Duval and Greene streets in Old Town Key West.
Sloppy Joe’s traces its official beginning to December 5, 1933, the day Prohibition was repealed. The establishment moved to its current Duval Street location in 1937.
The bar is known for its long Key West history, friendship between owner Joe Russell and Ernest Hemingway, prominent Duval Street location, live music and annual Hemingway Look-Alike Contest.
Yes. Hemingway was a friend, customer and fishing companion of owner Joe Russell during the author’s Key West years. Their friendship is central to the bar’s history and identity.
Sloppy Joe’s operated from the Greene Street building now occupied by Captain Tony’s Saloon before moving to 201 Duval Street in 1937. Sloppy Joe’s and Captain Tony’s are separate establishments today.
Yes. Sloppy Joe’s serves casual food, including its signature Sloppy Joe sandwich and other bar favorites. Review the current menu and kitchen hours on the official website before visiting.
Yes. Live entertainment is a major part of the Sloppy Joe’s experience. Check the official entertainment calendar for current performers and times.
Families may find daytime visits more suitable for lunch, sightseeing and history. The atmosphere becomes louder and more adult-oriented as evening entertainment and nightlife begin. Parents should use their judgment and confirm current policies.
Sloppy Joe’s is approximately half a mile from the Key West terminal, or about a 10-minute walk through the Historic Seaport and Old Town.
Sloppy Joe’s typically holds the contest in July as part of Key West’s Hemingway Days celebrations. Dates and entry details vary, so confirm the current schedule with the venue.
Hero Image Photo Credit: Historic Tours Key West