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The famous Sloppy Joe’s Bar is more than just a local watering hole where you can stop in for some live music, cold drinks and good food, it’s a Key West tradition. A gathering place where locals and visitors mesh, this well-known bar has hosted thousands of patrons through the years, the most celebrated being Ernest Hemingway. A visit to the Southernmost City is incomplete without a stop into Sloppy Joe’s Bar – but before you go, check out this guide.
The Bar’s History
Established on December 5, 1933, the day prohibition was repealed, Sloppy Joe’s was the brainchild of Joe Russell, an entrepreneur who was operating a local speakeasy at the time. Ernest Hemingway, a dear friend who was one of the many folks in town that viewed prohibition as ridiculous, was one of his customers who patronized his illegal operation when the need for scotch arose. At that time, the legendary watering hole was named The Blind Pig and was Russell’s first legitimate attempt as a saloon owner. He leased the run-down building for $3 a week and soon, the dive bar became a popular hang out for the island’s rowdier crowds. They could gamble, drink 15 cent whiskey and 10 cent shots of gin. Soon after, it was renamed The Silver Slipper.
It wasn’t long after that Hemingway convinced Russell to rename the bar once more, this time to honor a bar in Havana owned by Jose Garcia that sold liquor and iced seafood. Because of the intense Havana heat, the floor of the bar was always wet with melted ice. This caused customers to complain that Jose was running a sloppy bar. And thus, the name Sloppy Joe’s was born.
The Big Move…Down the Street
Originally located at 428 Greene Street, Sloppy Joe’s moved to the corner of Greene Street and Duval Street in 1937 when rent went up by $1 a month. And in true Key West fashion, the move didn’t stop or even slow down business, customers simply picked up their drinks and a piece of furniture and then carried it down the block to the new location. Soon, all of the bar stools and other furnishings arrived at the new address. Those who were regulars during that time period were lucky enough to sit across the bar from Hemingway and to be served by “Big” Skinner, Sloppy Joe’s celebrated bar tender whose personality was as big as he was. All 300+ pounds of him.
The new location had gambling and billiards in the back room and boasted the longest bar in town. The walls were adorned by large paintings of fighters and a 119-pound sailfish caught by Hemingway. Hanging on the wall these days, customers can see the bat that “Big” Skinner used to control the bar’s unruly customers.
Hemingway and Russell’s Friendship
Ernest Hemingway was more than an enthusiastic patron of Sloppy Joe’s Bar, he and Joe Russell were great friends and fishing buddies for 12 years. In fact, Hemingway used Joe as the model for the character Freddy of Freddy’s Bar in his acclaimed novel To Have and Have Not.
Hemingway, and what folks refer to as his “mob,” were regulars at Sloppy Joe’s. Mob members included locals John Dos Pasos, Waldo Pierce, J.B. Sullivan, Hamilton Adams, Captain Eddie Saunders, and Henry Strater. When you enjoy a cocktail at Sloppy Joe’s today you can see pictures of several of Hemingway’s catches as well as the sailfish that still hangs on the wall. It’s also home to the Ernest Hemingway lookalike contest that began in 1981.
Sloppy Joe’s Today
Added to the National Register of Historic Places in 2006, the legend of Sloppy Joe’s is still very much alive today. This popular Key West bar continues its tradition of quirky Conch ambiance, great food, live entertainment and of course, frosty and slushy cocktails.
The Hemingway lookalike contest has evolved into a weeklong celebration that includes tributes to the renowned author’s life, work and sportsmanship. Hemingway Days events include a short story competition, street fair and storytelling contest. The lookalike contest culminates the festival and is judged by Hemingway family members.
Whether you stop in for lunch or dinner, you’re in for a unique and unforgettable experience at this iconic Key West saloon.
Things To Do Nearby
As you can imagine, Sloppy Joe’s ideal location in the midst of all that’s happening on Duval Street means you can enjoy a myriad of activities and attractions within walking distance.
It took 17 years for Mel Fisher to finally find the mother lode, the priceless treasure that consisted of stacks of silver bars, silver coins, gold, jewels and thousands of magnificent artifacts from the Neustra Senora de Atocha. At this special museum, just a few minutes walk from Sloppy Joe’s, you can view many of these pieces up close and learn all about the treasure, the era of the pirates and much more.
Take a ride through history as you tour on the historic Conch Tour Train. This long-standing tour has been transporting guests since 1958 and takes you on a 90-minute journey through Key West’s rich past and most popular attractions.
Whether you enjoy the work of John James Audubon or strolling among thriving bromeliads, orchids and other tropical flowers, a visit to this historic house is sure to please. A short 5-minute walk from Sloppy Joe’s, the Audubon House features antique furnishings, some of Audubon’s renowned paintings and beautiful gardens.