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Plan Your Trip to Key West: Best of Key West Tourism

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This award is our highest recognition and is presented annually to those businesses that are the Best of the Best on Tripadvisor, those that earn excellent reviews from travellers and are ranked in the top 1% of properties worldwide.
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Explore Key West

Forever in holiday mode, Key West is all about kicking back. But it's not just a beach town. There's also history, culture, nature, and incredible diving and fishing. Stroll through historic Old Town to see the area's famous conch houses and where Ernest Hemingway used to live. Or take the ferry out to Dry Tortugas, a stunning, mostly underwater national park where you can snorkel with parrotfish and tour a Civil War site. Seafood and key lime pie are musts, but Cuban food is up there too (after all, Key West is just a stone's throw from Havana). Once the sun goes down (everyone watches from Mallory Square), head to Duval Street, a rowdy strip of bars and clubs, like the legendary Sloppy Joe’s. That’s not all there is to do—we've got more recs, below.

Travel Advice

Essential Key West

How to do Key West in 1 day

Fresh seafood, sunset boat rides, and fun dive bars
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Traveller Guides

A nightlife guide to Key West

Bar-hopping in Key West is quite the experience—it’s truly a come-as-you-are casual island where you can let it all hang out and just vibe. From divey bars loved by Hemingway to epic drag shows, and of course, cool craft cocktail bars, here’s my guide to a great night out.
Amber Love B, Miami, FL
  • Sloppy Joe's Bar
    Easily the most legendary bar in Key West, Sloppy Joe’s has been around since 1933 and was a favourite of Ernest Hemingway. I love popping in for conch fritters and a frozen Rum Runner and enjoying the live music from local bands that play every day until closing.
  • General Horseplay
    One of the newer cocktail-driven spots in town, General Horseplay is where to go for a well-curated menu, housemade syrups, and fat-washed cognacs. Vibes are on point and the bartenders are super knowledgeable and always down to experiment with your palette. Don’t miss the more casual backyard area with live music and games.
  • 801 Bourbon Bar
    It’s no surprise that one of the country’s most LGBTQ+ cities has a bar with a drag cabaret. Downstairs always has music and karaoke, but upstairs is where the real fun happens. There’s a nightly drag show that takes place in a small, but cosy room with super affordable drinks. A warning: If you sit near the stage, you will be participating in the show in a big way.
  • The Chart Room Bar
    This place is a hotel-room-turned-bar that’s been around for decades. It’s super small and the type of spot you stop into for a drink and free bar snacks. In the 1970s, a young Jimmy Buffet would play here regularly, in exchange for free drinks, while he workshopped songs that would later become some of his biggest hits.
  • Green Parrot Bar
    This is a true dive bar in every sense of the word. You won’t find fancy drinks or food, but you will find incredible live music and tons of people living their best Florida Keys life. The staff is friendly and quick which means you’ll be spending way more of your time people-watching and taking in the cool music memorabilia on the walls than you will waiting for a drink.
  • Rick's Key West
    If you’re visiting Key West with a group, this is your spot. Rick’s Bar is a real choose-your-own adventure situation with eight bars in one. The highlights: Durty Harry’s, which is a rock music venue pub-like room; Rick’s Loft, where you’ll find legit cocktails; and Rick’s Upstairs for nightclub dancing. And there’s way more.
  • 22&Co
    Flamingos, tutus, and unicorns—oh my. Totally different from any other bar in town, 22&Co is all about embracing fun, silly, colourful lifestyles and not taking anything too seriously. The drinks are on the sweet and fruity side, filled with edible glitter made by bartenders with big personalities who really love their job. There’s bingo, tarot card readings, and drag shows weekly. Protip: Show up in a tutu and you’ll score 22% off your bill.