Raise a Glass to Freedom: Key West’s ‘End of Prohibition Celebration’

Imagine stepping back into the roaring 1930s—a time of secret speakeasies, sultry jazz, and the audacious rebellion of America’s Prohibition era. From December 1–5, Key West invites you to do just that, in true island style, at the End of Prohibition Celebration hosted by the iconic Sloppy Joe’s Bar.

Why You Can’t Miss This Party

Sloppy Joe’s isn’t just a bar—it’s a legend. Once the watering hole for Ernest Hemingway and a hub for “imported” rum during Prohibition, this Key West staple breathes history, mischief, and more than a little rum-soaked charm. With its storied past as a speakeasy operated by Joe Russell—famed charterboat captain and rum-runner extraordinaire—it’s the perfect stage for celebrating the end of America’s dry spell.

Here’s why this festival should top your travel list:

Prohibition-Era Highlights

• Step Back in Time: Begin the celebration with a salute to Sloppy Joe’s very own Blonde Reserve Rum on Sunday, Dec. 1. Because what better way to toast history than with a cocktail in hand?
• Mixology Magic: Hone your speakeasy skills at the Prohibition Days Cocktail Class, Monday, Dec. 2, at the Hemingway Social Club. Bonus: a VIP tour of the Papa’s Pilar Distillery.
• Cinema Nostalgia: Tropic Cinema screens The Untouchables and De Palma, offering a cinematic dive into Prohibition's gritty, gangster-filled legacy.
• Deco Delights: The Repeal Party on Dec. 5 is the crown jewel of the festival. Dress in your 1930s finest, sip era-appropriate cocktails, and swing the night away with live bands, mixology shows, and prizes for the best costumes.

All the Fun, None of the Secrets

The festival peaks on Dec. 5—the 91st anniversary of the repeal of Prohibition—with a jubilant party that promises everything but discretion. Revelers can expect giveaways, spirited toasts, and jubilant celebrations kicking off at 5 p.m. in honor of the historic 21st Amendment.

Quick Tips for Your Trip

• Where: Sloppy Joe’s Bar, 201 Duval St., Key West, FL
• When: Dec. 1–5, 2024
• Don’t Miss: The cocktail class at Hemingway Social Club and the epic Repeal Party

Get Ready to Party Like It’s 1933!

Key West’s End of Prohibition Celebration is your passport to a bygone era of indulgence and rebellion, set against the vibrant backdrop of one of the most laid-back islands in the U.S. Whether you’re a history buff, a cocktail enthusiast, or just someone who loves a good party, this event promises an unforgettable mix of nostalgia, charm, and downright fun.

So what are you waiting for? Pack your flapper dresses, shine your Oxfords, and head to Key West to raise a glass to freedom—and maybe a second one to Hemingway. Cheers!

For event details, schedule, and tickets, visit KeyWestBootleggers.com.