May 2024 Newsletter

Sloppy Joe's Bar, Key West | May 2024
May Newsletter

Sloppy Joe's Bar, Key West | May 2024

Sloppy joe's bar building in key west

Sloppy Joe's Celebrates 87 Years on the Corner of Duval and Greene Streets

On December 5, 1933, a monumental day in history, Prohibition was repealed, and Sloppy Joe's Bar officially opened its doors. At that time, it was named the Blind Pig and was located at 428 Greene Street, just a hop, skip, and jump from our current location at the corner of Duval and Greene Streets. The Blind Pig was a doorless, run-down building that Joe Russell leased for three dollars a week. It had sawdust on the floor, pool tables, and gambling. The prevailing attitude was “come as you are and stay as long as you want,” literally, since it was open twenty-four hours a day.

The bar was destined to go through two name changes and a sudden change of location before it would become today’s Sloppy Joe’s Bar seen by millions of visitors to Florida’s southernmost outpost.

You can learn more about the colorful history of Sloppy Joe's Bar.

Sloppy joe's celebrates 87 years on the corner of duval and greene street
Saturday is caturday

May is for Moms!!

Join us every Saturday in May for Caturday with donations benefiting The Florida Keys Healthy Start Coalition. The Florida Keys Healthy Start Coalition unites people and resources to improve the health and well-being of pregnant women, children, and their families in the Keys. It is a system that guarantees that all women in the Florida Keys have access to prenatal care and that all infants have access to services that promote normal growth and development. The Coalition provides community oversight and planning to improve maternal and child health outcomes. Serving over 75% of the approximately 750 babies born in Monroe County every year. They work with women and families of all economic levels, with or without insurance.

For more information or to make a donation, please visit the Sloppy Joe's Foundation. Your generosity is appreciated!

Sloppy Joe's Cocktail of the Month

Pilar six-toed cat

Pilar Six-Toed Cat Recipe


  • Sloppy Joe's Blonde Reserve Rum by Pilar 1 oz.
  • Cointreau .05 oz.
  • Orange Juice
  • Splash of Cream
Sloppy joe's mercantile

Shop Authentic Sloppy Joe's Bar Key West Clothing and more!

Take a look inside our online store; we have new items to add to your Sloppy Joe’s t-shirt and tank top collection.

See what’s in our “on-sale” bin.

10% off online orders of $50 or more. Use code save10. Offer expires 5-31-24. Does not include gift cards.

Looking Back at the 28th Annual Key West Songwriters Festival

Key west songwriters festival playing at sloppy joe's
Key west songwriters festival stage in front of sloppy joe's
Key west songwriters festival concert in front of sloppy joe's
Hemingway look-alike contest


5:00 pm

Meet the “Papas” at Sloppy Joe’s. Get to know the contestants and previous winners of “Sloppy Joe’s Hemingway® Look-Alike Contest.


6:00 pm

Hemingway Look-Alike Society scholarship presentations. The society is to announce the winners of its annual scholarships for Florida Keys students. On stage at Sloppy Joe’s Bar.

6:30 pm

Sloppy Joe’s 43rd Annual Hemingway® Look-Alike Contest – Preliminary Round One on stage at Sloppy Joe’s.

FRIDAY, JULY 19, 2024

1:30 pm

“Papa” Hemingway Look-Alike Fish-Off. Cheer your favorites as the “Papas” compete in this dockside catch-and-release challenge using traditional “Cuban yo-yos” at Conch Republic Seafood Co. docks, 631 Greene Street.

6:30 pm

Sloppy Joe’s 43rd Annual Hemingway® Look-Alike Contest – Preliminary Round Two on stage at Sloppy Joe’s.



Photos with “Papas.” Hemingway® Look-Alikes provides a photo opportunity for fans. Happens on Greene Street next to Sloppy Joe’s Bar.

1:00 pm

Running of the Bulls. This wacky event, sponsored by Sloppy Joe’s Bar, features past “Papa” Hemingway® Look-Alike Contest winners dressed in their Pamplona best and a breed of “bull” found only in Key West. The fun takes place on Greene Street outside Sloppy Joe’s.

HLAS will sell red berets and red bandanas (limited quantities) beginning at 12 Noon on Saturday. Those wishing to wear traditional white clothing with a red sash need to be prepared and bring their own clothing (these items are not sold).

6:30 pm

Sloppy Joe’s 43rd Annual Hemingway® Look-Alike Contest – FINAL ROUND to name Papa 2024.

SUNDAY, JULY 21, 2024

9:00 am-1:00 pm

Papa Birthday Bash at Sloppy Joe’s! Bloody Marys with Papas, Photo Opportunities with Papa 2024, and Papa Birthday Cake at noon.

For complete details of the Hemingway Look-Alike Contest, visit

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