- Attraction: Sloppy Joe’s Bar
- Location: 201 Duval St, Key West, FL 33040
- Industry: Bar
- Website: https://sloppyjoes.com/
Picture this: you’re sitting at the same bar where Ernest Hemingway once held court, sipping a rum cocktail while live music fills the air and the energy of Duval Street pulses just outside the jalousie doors. Welcome to Sloppy Joe’s Bar, where literary history meets island time in the most authentic way possible.
Since December 5, 1933 – the very day Prohibition ended – this iconic establishment has been serving up more than just drinks. What makes this place truly special is its legendary midnight move in 1937, when owner Joe Russell and his loyal customers literally carried the entire bar down the block to avoid a $1 rent increase, never missing a beat in service.
Located at the bustling corner of Duval and Greene Streets since that famous relocation, Sloppy Joe’s isn’t just a bar – it’s a living piece of American literary and cultural history that continues to welcome locals and visitors with the same spirited atmosphere that captivated one of the world’s greatest writers.
Menu Highlights & Signature Eats
The Original Sloppy Joe Sandwich: This is the sandwich that made Sloppy Joe’s and Key West famous – delicious ground beef with celery, onions, and peppers in a sweet, flavorful tomato sauce. You’ll taste why this messy masterpiece has been a crowd-pleaser for nearly a century. The beef is tender and the sauce strikes that perfect balance between sweet and tangy.
Conch Fritters: These golden-brown Key West classics are crispy on the outside and tender on the inside, served with a zesty Key Lime sauce that adds the perfect citrus kick. You’ll understand immediately why locals and tourists alike consider these a must-try appetizer.
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Keep Exploring →Havana Nachos: Tortilla chips topped with black beans, onions, tomatoes, black olives, jalapenos, and cheddar jack cheese, served with sour cream and salsa. These aren’t your average nachos – they’re loaded high and perfect for sharing while you listen to live music.
The Famous “Full Moon” Fish Sandwich: Beer-battered, deep-fried fish smothered with peppers, onions, mushrooms, and cheese. You’ll get a massive sandwich that’s messy in all the right ways, with the crispy batter giving way to tender fish inside.
Wings That Pack Heat: Choose from Plain, Buffalo, Honey BBQ, or Garlic Parmesan varieties, served with celery sticks and blue cheese dressing. The Buffalo wings have just the right amount of kick, while the Garlic Parmesan offers a more mellow but flavorful option.
Cuban Sandwich: Traditional pressed Cuban bread with ham, Cuban pork, Swiss cheese, pickle, mustard and mayo. You’ll taste authentic Key West Cuban flavors in every bite, with the bread perfectly pressed and the pork seasoned just right.
Drinks & Signature Cocktails
Award-Winning Sloppy Rita: Made with Cazadores Reposado Tequila, Citronge, sour mix, orange juice and club soda, with a squeeze of lime. This isn’t your typical margarita – it’s smoother and more complex, with the orange juice adding a unique twist that sets it apart.
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Discover MorePapa Doble: Named after Hemingway’s favorite drink, this cocktail pays homage to the literary giant’s legendary thirst. You’ll experience a piece of history with every sip of this expertly crafted rum-based cocktail.
Sloppy Ginger: Made with Mutiny’s Ginger Turmeric infused Island Vodka, mint, lemonade & splash of club soda. The ginger gives it a warming spice that’s refreshing rather than overwhelming, perfect for Key West’s tropical climate.
Frozen Tropical Specialties: From piña coladas to rum punches, you’ll find expertly crafted frozen drinks that capture the essence of island life. The bartenders know how to make them strong enough to be satisfying without being overpowering.
Atmosphere & Entertainment
Historic Ambiance: The circa 1917 brick-and-stucco building features wood-paneled walls displaying Hemingway memorabilia, including a 119-pound sailfish he caught. You’ll feel the weight of history as you take in the well-worn wooden bar, vintage photographs, and authentic Key West décor that hasn’t been sanitized for tourists.
Live Music All Day: Live entertainment runs from 10 a.m. to 2 a.m. every single day, with performances at noon, 5:30 p.m., and 10 p.m. You’ll experience everything from acoustic sets during lunch to high-energy bands as the night progresses, with the music getting livelier as the sun goes down.
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Keep Exploring →Open-Air Island Vibe: The old jalousie doors can be thrown open to let in the Duval Street energy, creating that perfect indoor-outdoor Key West feel. You’ll enjoy the tropical breeze while still being part of the action inside.
Authentic Key Conch Character: The space feels genuinely lived-in rather than manufactured, with ceiling fans whirring overhead and that comfortable, unpretentious atmosphere that makes both locals and visitors feel at home. You’ll notice it’s larger inside than it appears from the street, but it still maintains an intimate, neighborhood bar feeling.
Other Considerations
Tourist-Friendly Pricing: While you’ll pay Duval Street prices, most visitors find the portions generous enough and the experience memorable enough to justify the cost. Expect to spend a bit more than you would at a typical local bar, but the historic significance and prime location make it worthwhile.
Crowd Dynamics: Yes, it gets crowded, especially when cruise ships are in town, but people come and go quickly so tables open up regularly. You’ll find the best times to visit are earlier in the day or late at night when the cruise ship crowds have dispersed.
No Reservations Needed: Just walk in and grab a table – the come-as-you-are attitude is part of the authentic Key West charm. You might have to wait briefly during peak times, but the turnover is steady.
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Discover MorePet-Friendly Policy: Like Key West itself, Sloppy Joe’s is dog friendly, and servers will gladly bring a water bowl for your four-legged companion. You can even order a doggie bag or snack for your pet.
Historic Significance: Sloppy Joe’s Bar is listed on the National Register of Historic Places, so you’re not just visiting a bar – you’re experiencing a piece of American cultural heritage that has remained authentic to its roots.
Extended Hours: Open Monday through Saturday from 9 a.m. to 4 a.m., and Sundays from 10 a.m. to 4 a.m. You can literally start your day here with morning drinks and end it in the early morning hours – it’s the perfect home base for exploring Duval Street.
Sloppy Joe’s Bar
📍 201 Duval St, Key West, FL 33040
