Key West's 'End of Prohibition Celebration' Set for Dec. 3-5

KEY WEST, Fla., Nov. 5, 2025 /PRNewswire/ -- During Prohibition, when the federal government imposed a nationwide ban on alcohol, defiant Key Westers smuggled liquor from Cuba and sold it in illegal watering holes called speakeasies. Wednesday through Friday, Dec. 3-5, libation lovers can celebrate the 92nd anniversary of Prohibition's 1933 repeal at Sloppy Joe's — the iconic Duval Street saloon founded by rumrunner and speakeasy owner Joe Russell.

Headquartered at the 201 Duval St. bar, the End of Prohibition Celebration marks both the revocation of the 1920-1933 alcohol ban and the birth of Sloppy Joe's. Events include three days of live entertainment, mixology demonstrations and classes, Prohibition-era film screenings, the unveiling of Sloppy Joe's Key West History exhibit wall, and a gala themed party and costume contest.

Sloppy Joe's is a fitting headquarters for the celebration, since it was opened by original owner Joe Russell on the day Prohibition was repealed. The bar's regular patrons included Ernest Hemingway and his local and literary cohorts.

As well as the alcohol ban, the Prohibition era encompassed cultural shifts in music, lifestyle and fashion. The period is characterized by the popularity of jazz and dances like the Charleston, the "flapper" subculture and a spirit of liberation — all represented in the End of Prohibition Celebration.

The festivities begin Wednesday, Dec. 3, with live entertainment from 10 a.m. to 2 a.m. and a salute to the anniversary of Sloppy Joe's signature Blonde Reserve Rum.

Nonstop live entertainment continues daily throughout the festival.

Both Wednesday and Thursday, Key West's Tropic Cinema will screen the Prohibition-era musical "Chicago," a stylized dark comedy that won six Academy Awards. The production stars Renée Zellweger, Catherine Zeta-Jones, Richard Gere and Queen Latifah. Showings are scheduled for 6 p.m. Wednesday and 5 p.m. and 7:15 p.m. Thursday at the 416 Eaton St. cinema.

Festival attendees also can enjoy a cocktail experience at the Hemingway Social Club at the Hemingway Rum Company, 201 Simonton St., and a hands-on rum-themed mixology adventure at Bar 1 at the Key West Cooking Show venue, 291 Front St.

The End of Prohibition Celebration's anticipated highlight is Sloppy Joe's Repeal Party on Friday, Dec. 5 — the 92nd anniversary of the ratification of the U.S. constitutional amendment that revoked the alcohol ban. Revelers are invited to party like it's 1933 and wear flapper dresses, fedoras and other garb recalling the period.

The event is hosted by Landon Bradbary. Attractions include live music by swing bands, a costume competition, an appearance by a vintage Anheuser-Busch delivery truck, giveaways and period cocktails.

During the 5 p.m. hour, when the repeal was finalized in 1933, festivities will commemorate the moment — and the birth of Sloppy Joe's — with the unveiling of a large-scale exhibit wall of vintage photographs, some never before displayed, that document Key West's colorful history.

For information, a festival schedule and ticketing links, visit https://keywestbootleggers.com.

Media Contact: Carol Shaughnessy
Phone: 305-797-0579
E-mail: [email protected]

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SOURCE Key West End of Prohibition Celebration