KWGuide

The Best Bars In Key West

Dive bars, waterfront spots, and places where Hemingway probably punched someone.
The Best Bars In Key West image

photo credit: Iris Moore

If finding a great bar in Key West seems daunting, it’s only because the island can feel like one never-ending bar. On seemingly every block, you’ll find chairs with waterfront views, stools within earshot of someone strumming an acoustic guitar, and places that claim to have hosted Ernest Hemingway. The good news is that there aren’t any bad choices when going out in Key West. Just keep your drink orders simple, because cutting-edge cocktails aren’t really a thing here. And know that Duval Street, often called Key West’s Bourbon Street, is where you’ll find the most (and rowdiest) bars. 

If the thought of taking shots with wandering bachelor parties makes you shudder, though, this guide has plenty of options off Duval, with all the Jimmy Buffett vibes that made you book a room here in the first place. And when you get hungry, check out our guide to the best restaurants in Key West.


THE BARS


photo credit: Iris Moore

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Bar

Key West

$$$$Perfect For:Live MusicClassic Establishment
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If there is one bar that represents everything great about going out in Key West, it’s Green Parrot. This place has all the Keys nightlife staples: excellent nightly live music, a wooden interior that’ll make you feel a little like a pirate, and bar seating that makes it easy to befriend strangers. This place is a well-deserved classic, and it’s just as fun at 2pm as it is at 2am. The building has been standing since the late 1800s and if you’d like to know what the scene looks like before you go, they have a live webcam streaming all day, every day.


This is the most famous, crowded, and historic bar in Key West. And yes, it’s worth stopping in for a frozen rum runner. Sloppy Joe’s is such an institution because Hemingway himself spent many years here drinking way too much and probably getting into a lot of fights. Today, it’s a little tamer, undeniably touristy, but still fun if you don’t mind big, loud bars. There are usually live bands playing cover songs that are easy to scream along to (a man named Gerd Rube was crushing it during our last visit). But if you want to avoid the more rambunctious Duval Street crowds, go around lunch (or check the bar’s live webcam before you go). Also, if you happen to be visiting around July 18, please come here for the annual Hemmingway look-alike contest.


After you’re done at Sloppy Joe’s, walk across the street to Captain Tony’s if you love a historic bar with a juicy backstory. This was actually the original Sloppy Joe’s, but legend has it that after a landlord dispute, the bar and its regulars packed everything up in the middle of the night and walked it across the street to the new Sloppy Joe’s. (Hemingway apparently thought this was hilarious). Captain Tony’s isn’t as energetic as Sloppy Joe’s, but it’s one of those old dark bars wallpapered in wrinkly dollar bills that feels so uniquely Key West. Ask the bartender about the building’s history as the city morgue if you’re feeling brave.


Key West bars, especially the popular ones, can get crowded. So if you’re looking for somewhere to escape—and if you generally prefer drinking at a dive bar—go seek shelter at Chart Room. This Key West staple is impossible to stumble upon unless you know about it, as it’s located inside a bougie resort, but completely open to the public. Every inch of the small room is covered in a flag, photo, or bumper sticker, and it’s quiet enough for a conversation or a game of backgammon over a very tasty Old Fashioned. Also, there are complimentary peanuts and hot dogs for anyone brave enough to reach into the slow cooker.


It might come as a surprise to folks visiting from landlocked states where even a large puddle feels exciting, but Key West isn’t necessarily a beach destination. Most of the action happens on asphalt. If this news makes you angry, you should visit Lagerheads, one of the only true beach bars in Key West that is literally located on a (small) beach. Hang out in the little wooden shack where you’ll find the bar, or rent a beach chair for $10 and drink with your toes in the sand. It’s idyllic either way, and there’s a musician strumming between Pink Floyd and Grateful Dead songs to make it even more difficult to leave.


Schooner Wharf has every trait of a great Keys bar: a waterfront view, live music, cluttered wooden decor, and no shortage of grey-haired men wearing shirts with goofy slogans about drinking. It’s a great place to have a few beers during sunset, but try to get a seat on the second-floor patio if the view is your main priority. If it’s live music you’re after, look for a table near the stage, where you can relax and place your drink order with one of the servers darting around.


LGBTQ culture is foundational to Key West, especially its nightlife. That’s why drag is big on the island, and the best (and rowdiest) place to partake is at 801 Bourbon Bar: a gloriously pink building that hosts the most fun drag show in Key West. The ticketed performance happens upstairs, on a small stage in a cramped room, and it’s a hilarious evening where you might very well become part of the performance if you’re sitting close enough to the stage. It's 18 and older before 10:30pm, and 21 and up after for reasons that will become obvious approximately five seconds into the show.


photo credit: Iris Moore

$$$$Perfect For:Live Music
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Every night, the lobby of the La Te Da Hotel turns into a little piano bar with strong martinis and no cover from 8:30-11:30pm. It looks small and unassuming from the street, but there’s always something fun happening inside, even if no one is technically playing the piano. The house acts usually consist of a trio of very talented vocalists who belt out cover after cover until, eventually, it turns into a little dance party. If you want even more spectacle and pageantry, you can buy a ticket for La Te Da’s cabaret show, a night of musical impressions by drag performers.


Sure, you could snack on peel-and-eat shrimp any time of day here, but the real reason you’re coming is all in the name. The sunset view looks like it could be on an actual postcard, and there’s a line of waterfront stools that give you an uninterrupted view. This place fills up fast between November and February, so if you're in town for the winter, try to show up with enough time before the sun clocks out to snag a good seat. If you can’t, that’s OK. They have a little side bar that’s accessible from Mallory Square, so you can grab a beer, and watch the sunset with the rest of the crowd.


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