Sloppy Joe’s Bar – Key West

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Sloppy Joe’s Bar – Key West

Sloppy Joe’s Bar

Sloppy Joe’s Bar in Key West, Florida, is an iconic establishment steeped in history and renowned for its vibrant atmosphere, live music, and strong ties to literary legend Ernest Hemingway. Located at 201 Duval Street, Sloppy Joe’s has been a cornerstone of Key West’s nightlife since its inception on December 5, 1933, the day Prohibition ended. Its origin, however, dates back to an earlier establishment known as the Blind Pig, a modest speakeasy operating on Greene Street.

The bar’s founder, Joe Russell, was a charter boat captain and rum-runner who capitalized on the end of Prohibition to open a legitimate establishment. When he relocated his business to Duval Street in 1937, the bar adopted the name “Sloppy Joe’s,” a moniker inspired by a bar in Havana, Cuba, that was known for its casual, unpretentious vibe. Russell’s bar quickly became a favorite haunt of locals, fishermen, and tourists alike.

History

Sloppy Joe’s most famous patron was undoubtedly Ernest Hemingway. The celebrated author made Key West his home during the 1930s and formed a close friendship with Joe Russell, who often took Hemingway on fishing trips. Hemingway’s presence at the bar added to its allure, and his legacy is still strongly felt today. Visitors can see memorabilia related to Hemingway and even participate in the annual Hemingway Look-Alike Contest, held during the Hemingway Days Festival every July.

The bar’s enduring charm lies in its lively ambiance and commitment to providing great entertainment. Sloppy Joe’s boasts a spacious, open-plan layout with a large stage that hosts live music every day of the year. Bands and solo artists perform a mix of rock, blues, country, and island tunes, ensuring there is something for everyone. The dance floor is often packed with revelers enjoying the rhythms and the camaraderie that Sloppy Joe’s fosters.

In addition to its entertainment, Sloppy Joe’s is renowned for its menu of classic American bar food and tropical drinks. Signature dishes include the Sloppy Joe sandwich, a nod to its namesake, as well as conch fritters, fish tacos, and burgers. The drink menu is extensive, featuring everything from frosty margaritas and mojitos to a selection of craft beers and the infamous “Papa Dobles,” Hemingway’s favorite cocktail, made with rum, lime juice, and a touch of grapefruit.

Sloppy Joe’s also plays a significant role in the community, hosting various events and fundraisers throughout the year. One of the most popular events is the annual New Year’s Eve celebration, which features a “Dropping of the Conch Shell” at midnight, a quirky twist on the traditional ball drop that draws crowds from across the island and beyond.

Conclusion

The bar’s rich history, vibrant atmosphere, and deep connection to Key West’s cultural fabric make Sloppy Joe’s more than just a place to grab a drink. It is a symbol of the island’s free-spirited, eclectic character and a must-visit destination for anyone exploring Key West. Whether you’re following in the footsteps of Hemingway, dancing to live music, or simply enjoying a cold drink in the warm Florida sunshine, Sloppy Joe’s Bar offers a unique and memorable experience that captures the essence of Key West.

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