Key West was once a land of pirates, wreckers, speakeasies, and rum runners. It shouldn’t come as a surprise that there are a lot of great bars in Key West.
Today, Key West is a popular haunt for those in search of fantastic nightlife. If it’s your first time in Key West, let us show you around our favorite places to grab a drink!
Follow in the footsteps of Hemingway or create your own bar-hopping route around the island. You probably can’t visit every bar in Key West, but you’ve got to check out a few on this list!
Key West Pub Crawl
If it is your first time in Key West, we suggest joining this Key West Pub Crawl. It will give you the lay of the land and include five drinks, and you’ll probably make a few friends to join you out later that night.
1. Sloppy Joe’s
Sloppy Joe’s is one of the most famous bars in Key West. It’s best known as the favorite watering hole of novelist Ernest Hemingway. Hemingway was even responsible for the name Sloppy Joe’s.
The owner, Joe Russel, was a boat captain and friend of Hemingway. Hemingway had suggested that Joe change the name to Sloppy Joe’s after a bar in Havana.
Sloppy Joe’s is a Key West staple and one of the most popular bars in Key West. It’s always busy, even on a random Monday night. It’s one of Key West’s premium entertainment bars, with live music until 2 a.m.
If you’re in the mood to dance, you’ve got to head to Sloppy Joe’s. The dance floor opens at 9:30 pm and soon fills with revelers, both locals and tourists.
Visiting Sloppy Joe’s is one of the things to do in Key West on everyone’s list, whether it is for a drink or a sandwich. If you are traveling with kids, coming during the day is no biggie. We have brought both our young children in.
If you’re in Key West and hear about the Hemingway Contest, you’ve got to check it out. This is a contest to find the best Hemingway look-alike. White-bearded Hemingway hopefuls line up and compete in challenges all to win the coveted prize… A Hemingway trophy! This competition has been running since 1981 and is a real crowd-pleaser.
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- Address: 201 Duval Street, Key West
2. Sunset Pier
Sunset Pier is quintessentially Key West. It’s the type of place you’d envisage relaxing and sipping on cocktails before you arrive. At Sunset Pier, you can do just that.
With views of the Gulf of Mexico, Sunset Pier is a go-to place for seafood, sunset, and tasty drinks. It is one of our favorite Key West restaurants on the water.
It’s one of the best bars in Key West for cocktails. Mojitos, margaritas, frozen cocktails, and other tropical drinks, they’ve got them all. They even have 12 craft beers to choose from.
Sit on colorful bar stools and watch a beautiful Key West sunset.
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- Address: 0 Duval Street, Key West
Related Article: Best Seafood in Key West
3. Hog’s Breath
The Hog’s Breath has a vibrant biker bar feel. There are always live bands playing good music, bikini contests, and plenty of good drinks. This is one of the best bars where there’s always something going on.
If you’re a newbie to Key West, you’ve got to try their Key Lime Pie shooter. Get all that delicious zesty goodness, but in alcohol form. What could be better?
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- Address: 400 Front Street, Key West
4. The Green Parrot
The Green Parrot has been part of Key West’s landscape for more than 125 years. This is a local’s bar, but the nightly happy hour attracts tourists too.
The Green Parrot is also afforded the title of ‘Last bar on U.S. Highway 1’. The bar is decorated with random historical objects, an assortment of junk, and memorabilia. This makes for an interesting visit, as you constantly spot different things.
The Green Parrot is arguably the best dive bar in Key West and one of the best Florida Keys bars. It’s one of the best spots for live music, which is on daily. From jazz and reggae to rock, there is something for every music taste here.
The last time we were here, I was pregnant, and the bartenders were so great they made me a really good virgin mojito.
- Website
- Address: 601 Whitehead Street, Key West
5. Captain Tony’s
The oldest bar in Key West and the oldest bar in Florida, Captain Tony’s is must visit spot. Captain Tony’s is an old-school pub and Tennessee Williams’ favorite watering hole.
Captain Tony was a fishing boat captain, casino operator, and former Mayor of Key West. Built in 1851 as an icehouse, this bar is steeped in history.
One of the first things you’ll notice as you enter is the ceiling. It is covered in hundreds of business cards, license plates, and bras! It seems women visiting Captain Tony’s have tended to lose all their inhibitions.
Enjoy beers at the bar and the great variety of quality live music each night.
- Website
- Address: 428 Greene Street, Naval Air Station, Key West
6. Bull & Whistle
Another of Key West’s bars on Duval Street is the Bull & Whistle. The Bull & Whistle offers a casual atmosphere and a 3-in-1 bar experience.
There’s a large central bar with a stage. The second floor is where the Whistle is located. The Whistle is a sports bar with pool tables, darts, and games.
One of the best things about this bar is the second-floor veranda. Grab a drink and see which Duval Street bars people are heading to. The final bar is the Garden of Eden.
This is one of the most unique bars in Key West, but more on that later. With so many elements, the Bull & Whistle is perfect for groups of friends.
- Website
- Address: 224 Duval Street, Key West
7. Smallest Bar in Key West
This is one of the Duval Street bars you’ll probably just walk past. That’s because this place is just 72 square feet, hence why it is called the Smallest Bar in Key West.
This is an ideal spot to go to with friends because you’ll have the whole bar to yourself. There are only a couple of bar stools and no room for more than ten people.
Cram yourselves into this tiny bar, and you might just attract a tourist or two! It’s probably a given to say, but head there early, or else they’ll be full.
- Address: 124 Duval Street, Key West
8. Tipsy Rooster
The Tipsy Rooster is a cute little bar and liquor store. If you’re searching for a relaxed open-air bar, then head to the Tipsy Rooster. It is one of our favorite places to just chill with a nice beverage in hand.
They serve up delicious craft cocktails, including a Key Lime Pie Pina Colada that’s seriously tangy. Opt for a beer or rum and tuck into one of their delicious pizzas. If you’re passing by the Tipsy Rooster, grab some drinks —there’s even live music.
- Website
- Address: 1325 Simonton Street, Key West
9. Garden of Eden
Of all the best bars in Key West, the Garden of Eden is the most eye-opening! Sitting on top of the Bull & Whistle, this is a “clothing optional” bar. You’ve heard of a nudist beach, but what about a nudist bar?
Tall jungle-link plants line the walls, so no one wandering along Duval Street can see. There is also a no-photography rule that’s strictly enforced. This includes no cameras and no phones.
There are shirtless bartenders and fully nude individuals tanning in the Key West sun. Enjoy a cocktail and get rid of those unwanted tan lines right in the heart of Duval Street.
- Website
- Address: 224 Duval Street, Key West
10. The Rum Bar
If you visit Key West and love rum, this is the perfect bar for you. Part of The Speakeasy Inn, The Rum Bar is super laid-back and friendly. Of the best bars in Key West, rum aficionados will revel over this place.
They have more than 350 rums — yes, you read correctly! That’s a lot of rum to choose from. If you can’t decide, why not opt for their rum flight? As well as rum runners, they also have tropical cocktails and mojitos.
There’s good music, incredible rum, and plenty of good conversation at this Duval Street bar.
- Website
- Address: 1115 Duval Street, Key West
11. The Original Jimmy Buffet’s Margaritaville
Jimmy Buffet arrived in Key West in 1971 from Nashville. Many believe Key West was where he found his true voice as a singer. This Key West bar was the first of Buffet’s Margaritaville bar restaurants.
It’s been open since 1985 and is one of the best bars on Duval Street. Of course, the bar is named after Buffet’s famed 1977 song, Margaritaville.
Inside, there’s a big stage where local, national, and international bands perform. The place is filled with tiki bar decor, giving it an irresistibly tropical vibe. Grab drinks, conch fritters, a slice of Key Lime Pie, and enjoy your evening.
We aren’t usually chain bar and restaurant patrons, but the OG Margaritaville is worth a stop for a photo and drink. We wouldn’t eat a meal here. There are better local options; check out our best restaurants in Key West guide.
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- Address: 500 Duval Street, Key West
12. Flying Monkey
Flying Monkey is another of the famous bars in Key West. They are renowned for their frozen cocktails, which pack a real punch. Their frozen cocktails taste so good because they’re made from all-natural ingredients.
Stop by the Flying Monkey for a casual lunch or dinner, or cocktail. It’s super chill and one of the best outdoor bars in Key West.
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- Address: 227 Duval Street, Key West
13. Hank’s Hair of the Dog
Hank’s is a fantastic open-air bar. Sometimes it feels like a shame to be inside during Key West’s endless summer. Their daily 4-6 p.m. Happy Hour draws in the crowds.
Make sure you try Hank’s Tiki Punch for a delicious, fruity spiced rum drink.
As well as their tasty drinks, they also serve up some great food. Garbo’s Food Truck serves Hank’s customers some of the best food around. Garbo’s was even featured on Diners, Drive-In’s & Dive’s.
They’ve got all the necessary food needed to nurse a hangover. Their burgers, hot dogs, tacos, and burritos are out of this world.
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- Address: 409 Caroline Street, Naval Air Station, Key West
14. Smokin Tuna
This place has the feel of a beach bar but is still located on Duval Street. This is one of the best bars in Key West for an open-air atmosphere.
Order a frozen cocktail served in a souvenir cup and sit and enjoy the outdoor patio. Live music only adds to an already calming ambiance.
Of course, no visit to Smokin Tuna is complete without trying a tuna dish. If you’re a fish lover, you’ll love Smoking Tuna. They have Tuna Nachos, Tuna Melts, and the Florida Keys’ favorite conch fritters. There are also some non-fish options for those who don’t fancy tuna.
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- Address: 4 Charles Street, Duval Street 200 Block, Key West
Related Article: Best Beaches in Key West
15. Durty Harry’s
Durty Harry’s is one of the best bars on Duval Street in peak season. Durty Harry’s is known for its live music, which comes almost exclusively from The DurtBags.
This live rock music venue is hard to beat. It’s one of the best Florida Keys bars if you’re a rock lover.
The DurtBags cover tons of songs, except “Freebird” — you’ll have to tip $400 for that. Many have labeled The DurtBags as the best rock cover band in Florida.
Aside from the live music, you can enjoy the sports bar vibes and buzzing atmosphere.
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- Address: 202-208 Duval Street, Naval Air Station, Key West
16. Little Room Jazz Club
This jazz club in Key West is the perfect escape from the noise and bustle of Duval Street. The Little Room Jazz Club has an eclectic range of talented musicians. If you’re a jazz lover, you cannot miss a trip to this bar.
Enjoy a bourbon and an unrivaled atmosphere for dancing the night away. People usually stumble upon this bar, but it ends up becoming their favorite spot.
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- Address: 821 Duval Street, Key West
17. Waterfront Brewery
This place is ideal for tasting your beer, not just knocking back the bottles. The Waterfront Brewery has 12 delicious and unique beers on tap.
Beers include the American Amber, Island Life Lager, and even a Key Lime Pie. No, not the dessert; this is Key Lime Pie beer. If you are on the hunt for the real deal, here are the best places for Key Lime Pie in Key West.
I know that Key West locals love their Key Lime Pie, but really, a beer? Made with Key Lime juice, this beer is slightly tart with a lasting vanilla finish.
Go on. You’ve got to give it a try. If you can’t decide on a beer, why not order a craft beer tasting flight?
Sit at a sea view table and enjoy good food and unique locally crafted beers. If you’re looking for somewhere more relaxed, Waterfront Brewery is the place to be.
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- Address: 201 William Street, Key West
18. El Mason De Pepe
This is the best bar in Key West if you want Cuban food and drinks. El Mason’s patio is the ideal setting to enjoy one of their Caribbean cocktails. Views of Mallory Square and the Gulf of Mexico make for an entertaining location.
El Mason De Pepe is a vibrant celebration of all things Cuban and the best place for Cuban food in Key West. It’s the perfect bar for couples or groups. Make sure you arrive with an appetite because the food is top-notch.
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- Address: 410 Wall Street, Key West
Related Article: Miami to Key West Epic Road Trip
19. Key West First Legal Distillery
This distillery offers free 20-minute tours and free rum samples. That’s reason enough to go. While on tour, learn about Key West’s history and, of course, rum.
Their rum is gluten-free, vegan-friendly, and all-natural. If you want a quieter bar to really enjoy your drink, head to this local distillery.
- Website
- Address: 105 Simonton Street, Key West
FAQ Key West Nightlife
Does Key West have good nightlife?
Key West isn’t just somewhere to soak up the sun and eat Key Lime Pie. Key West has a reputation for offering visitors an unparalleled nightlife scene.
Nearly every place you look, there’s a lively joint waiting to be explored.
There would be no nightlife in Key West without the bars on Duval Street. Enjoy live music, frozen cocktails, and cold beers. These Key West bars are also some of the best Florida Keys bars.
What is the main bar street in Key West?
Duval Street is Key West’s epicenter and accounts for most of the bar scene for nightlife in Key West. It is almost impossible to visit Key West without hitting up Duval Street. It’s crammed full of restaurants, bars, and history.
Many bars on Duval Street were popular haunts of Ernest Hemingway and Tennessee Williams. There’s something for everyone at these Duval Street bars.
There are historic watering holes, jazz clubs, rum bars, and even a clothing-optional bar!
Can you drink alcohol on the street in Key West?
Many people think you can drink alcohol on the streets of Key West. WRONG, you cannot drink on the street in Key West.
According to the Key West Municipal Code, containers of alcoholic drinks in public are prohibited. Keep your drinking inside, or check out one of the open-air bars on this list.
What time do bars close in Key West?
Most bars in Key West close at 2 a.m. Sunday through Thursday, and some bars in Key West close at 4 a.m. on the weekends.
How old do you have to go into bars in Key West?
If a bar in Key West serves food, you are allowed in a bar at any age. Once the bar stops serving food, anyone under the age of 21 has to leave.
What is the drinking age in Key West?
Just like the rest of the United States and all of Florida, the drinking age is 21 in Key West.
If you are visiting from another country where you can legally drink, you have to follow the local drinking laws. Every bar in Key West will ask you for an ID. You will have to present a driver’s license or passport.
Best After Bar Food in Key West?
We often head to Mr.Z’s for some of the best pizza in Key West. For some reason, pizza is the perfect after-bar food. If you stay up SUPER late and watch the sunrise, here are the best places for breakfast in Key West.
What do you think is the best Key West bar?
We are always looking for new Key West nightlife places to check out!
Pin this list of best bars in Key West for your next trip!
