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Sloppy Joe’s Bar


Sloppy Joe’s Bar
Library of Congress
Sloppy Joe’s Bar started out as an illegal speakeasy during the Prohibition era, but later went legal once Prohibition ended. Author Ernest Hemingway was a frequent customer, along with his group of colorful friends known around town as “The Mob.” Sloppy Joe’s Bar is still a popular spot for locals, as well as visitors to Key West who come to see the place where Hemingway liked to have fun. Don’t miss it in July, when it is overtaken by Hemingway Look-a-likes.

History of Sloppy Joe’s Bar

Sloppy Joe’s opened officially on December 5, 1933, the day that the U.S. experiment in Prohibition came to an end. At the time it was called the Blind Pig, and owner Joe Russell had already been operating it an illegal speakeasy. Author Ernest Hemingway was a frequent patron of the bar, and a friend to Joe Russell. The bar, now operating legally, added a dance floor and renamed it the Silver Slipper. Hemingway encouraged Russell to change the name a third time, to Sloppy Joe’s, and this time the name stuck.

On May 5, 1937, the bar moved across the street to the corner of Greene and Duval, where it still stands today. The new location offered the longest bar in the city, and was a local favorite for affordable drinks and gambling. Hemingway brought his “Mob” of friends with him to the bar frequently. The rowdy group included John Dos Pasos, Waldo Pierce, J.B. Sullivan, Hamilton Adams, Captain Eddie Saunders, and Henry Strater.

Learn more about the Ernest Hemingway Home and Museum in Key West.

Visiting Sloppy Joe’s Bar

The bar is open daily until 4 am, and there is always something going on. There are live music performances every night, ranging from bluegrass to rock. Annual events include the Dropping of the Conch Shell on New Year’s Eve, the Put-In-Bay Music Festival in the spring, and the Hemingway Look-a-like Contest every summer.

The menu includes traditional Key West favorites such as conch fritters and Key Lime pie, along with a selection of appetizers, burgers, sandwiches, salads, wraps and pizza. The bar offers plenty of tropical drinks, such as rum runners, mojitos, and daiquiris, plus wine and draft or bottled beers. No one under 21 years of age is allowed in the bar after 9:30 pm.

And we can’t forget about the retail store, which carries over 300 products with the Sloppy Joe’s logo. You can pick up clothing items, shot glasses, beer mugs, or many more items to take home as souvenirs. There is also a web store, where you can place orders online to be shipped to you.

Sloppy Joe’s Bar is always a stop on the Best Tours of Key West.

Hemingway Days

Hemingway Days takes place in Key West every July, and draws Hemingway fans from all over the world. This fun festival started out in 1981 at Sloppy Joe’s Bar. The festival has since expanded to various locations and now includes literary events and contests, the “Running of the Bulls,” and a 3-day marlin fishing tournament. But most fun is perhaps the Hemingway Look-a-like Contest, which still takes place at Sloppy Joe’s. Stocky, tanned men with white hair and beards take over Duval Street for this fun competition.

Learn more about Hemingway Days in Key West.

More About Sloppy Joe Russell

Joe Russell was a charter boat captain, rumrunner, and served as Ernest Hemingway's boat pilot, friend, and frequent fishing companion. Hemingway used him as the model for Freddy, the owner of Freddy's Bar and captain of the Queen Conch in his novel To Have and Have Not. Joe Russell died in 1941 of a heart attack, and the age of 53.

Sloppy Joe’s Bar Contact Info

  • Address: 201 Duval Street, Key West
  • Hours: Open 365 days per year, from 9:00 am to 4:00 am. (Sunday hours are 12 Noon to 4:00 am.)
  • Web Site: http://www.sloppyjoes.com
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