Key West End of Prohibition Celebration
December 3 - 5, 2025
Sloppy Joe's Bar, Key West, FL
Take a step back into old Key West and celebrate the end of Prohibition with three days of fun-filled Prohibition-themed Films, Cocktails, History, Live Entertainment, and, of course, a blowout Party at Sloppy Joe’s! It is a true celebration of not only Key West’s but America’s most iconic eras.
Don’t miss the opportunity to dust off your Flapper Dresses and Fedoras for the swellest Costume Party since 1933.
History of Prohibition
Prohibition in the United States was a nationwide constitutional ban on the production, importation, transportation, and sale of alcoholic beverages from 1920 to 1933. The movement for Prohibition gained momentum in the late 19th century, driven largely by the temperance movement, which sought to reduce alcohol consumption due to its perceived role in social ills such as crime, domestic violence, and poverty. Organizations like the Anti-Saloon League and the Woman’s Christian Temperance Union lobbied for laws to restrict alcohol. Their efforts culminated in the ratification of the 18th Amendment in 1919, which prohibited the manufacture and sale of alcohol. This was further enforced by the Volstead Act in 1920, which provided legal mechanisms for enforcement.
However, Prohibition led to several unintended consequences, including the rise of organized crime. Bootlegging and the illegal production of alcohol became widespread, with gangsters like Al Capone profiting from the illicit trade. Speakeasies—secret bars where alcohol was sold—flourished, and many Americans continued to drink despite the ban. Public opposition to Prohibition grew over time as the government struggled to enforce the law and the social benefits promised by temperance advocates failed to materialize.
In 1933, Prohibition was officially ended with the ratification of the 21st Amendment, making it the only constitutional amendment to be repealed in U.S. history.
Celebration Schedule
Wednesday, December 3, 2025
Key West End of Prohibition Celebration Kick-Off Red & Gold Speakeasy Soiree – Sloppy Joe’s 201 Duval Street
- Join us as we celebrate the colorful history of prohibition times. Get in the spirit and dress to impress in your best Red & Gold finery.
- Donate & get your Prohibition Pearls benefiting The Sloppy Joe’s Foundation.
- Live Entertainment & fun all day starting at 10 am
- Sloppy Joe’s Blonde Reserve Rum Anniversary ~ Celebrate with a Prohibition Punch featuring Sloppy Joe’s Blonde Reserve & take home your own bottle available exclusively at Sloppy Joe’s.
Prohibition Era Film Pairing
6 p.m. “Chicago”
Tropic Cinema, 416 Eaton St.
This Prohibition-era musical spotlights Roxie Hart and Velma Kelly, both jailed for murder in 1920s Chicago, who connive to become famous with the help of lawyer Billy Flynn. A stylized dark comedy that won six Academy Awards, “Chicago” features brilliant performances by Renée Zellweger, Catherine Zeta-Jones, Richard Gere, and Queen Latifah.
Thursday, December 4, 2025
A Rum Cocktail Adventure – Key West Cooking Show: 291 Front Street, Suite 207 Upstairs
- 2:00 – 3:00 p.m.
Discover the spirit that gave Prohibition-era rumrunners their name. Learn about rum’s history and influence, and the secrets to creating classic rum cocktails, in a hands-on libation experience. Mix, shake, sip, and enjoy!
Reservations required; visit www.keywestcookingshow.com
Key West End of Prohibition Celebration – “The Best Party In Town” carries on! – Sloppy Joe’s: 201 Duval Street
- Live Entertainment all day, starting at 10 am
Prohibition Era Film Pairing
5 p.m. & 7:15 p.m. “Chicago”
Tropic Cinema, 416 Eaton St.
This Prohibition-era musical spotlights Roxie Hart and Velma Kelly, both jailed for murder in 1920s Chicago, who connive to become famous with the help of lawyer Billy Flynn. A stylized dark comedy that won six Academy Awards, “Chicago” features brilliant performances by Renée Zellweger, Catherine Zeta-Jones, Richard Gere, and Queen Latifah.
Friday, December 5, 2025
Key West End of Prohibition Celebration– Repeal Party – Sloppy Joe’s: 201 Duval Street
- Party like it’s 1933! Celebrate the 92nd Anniversary of the End of Prohibition! Dress to the nines in Black & Silver; drape your flapper self in diamonds, pearls, sequins, and splendor with host Landon Bradbary. Contests, Good Times, Legal Drinks & Giveaways. Special Appearance from the Anheuser-Busch Antique Truck. Don’t miss the 5 o’clock hour Repeal festivities.
- Live Entertainment & fun all day starting at 10 am
Images from the 2024 Key West End of Prohibition Celebration
Proud Supporting Sponsors
Key West End of Prohibition Celebration:
December 3 – 5, 2025
Sloppy Joe’s Bar
201 Duval Street, Key West, FL 33040
Info@KeyWestBootleggers.com
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