MyBartender > Places > Florida > Key West > Grab a Drink at These Key West Bars

Grab a Drink at These Key West Bars

Key West, Florida, is an exciting and eccentric city with a storied history and fantastic nightlife. Notable people, from author Ernest Hemingway to President Harry Truman, have called the small waterfront city home at some point.

people walking to popular bars on duval street in key west

Tourists from across the world visit Key West to engage in watersports, see the manatees, try the key lime pie, and visit some of the best bars in Key West, Florida!


Green Parrot Bar

601 Whitehead St, Key West, FL 33040
Phone: (305) 294-6133
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The Green Parrot Bar is housed in one of the oldest venues on the island. It’s located down the side street, just a few minutes walk from the busy Duval Street. Just look for the green light outside.

Once, it stood as a grocery store, but as the great depression hit the mainland, even Key West made some changes.


Capt Tony’s Saloon

428 Greene St, Naval Air Station Key West, FL 33040
Phone: (305) 294-1838
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Captain Tony’s is the oldest bar in Florida. The bar is a traditional pub and Tennessee Williams’ favorite place to find a drink. The bar’s namesake, Captain Tony, was a fishing boat captain and former Mayor of Key West.

As you enter or exit, try throwing a quarter into the mouth of the fish above the door; the rumor is that good luck will follow you while you stay in Key West.


Sunset Pier

0 Duval St, Key West, FL 33040
Phone: (305) 296-7701
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Sunset Pier offers a relaxing atmosphere and tropical cocktails to enjoy. It is located in Ocean Key Resort and Spa.

Sunset Pier offers views of the Gulf of Mexico and is one of the island’s hot spots for watching the famous Key West sunset. Try the mojitos or margaritas and enjoy some of the bar snacks.


The Rum Bar

1115 Duval St, Key West, FL 33040
Phone: (305) 296-2680
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Located in the Speakeasy Inn, The Rum Bar is located at the upper end of Duval Street. Try a flight of rum shots or the infamous rum runner.

The Rum Bar has a literal history of alcohol smuggling during prohibition–it is one of the only homes in Key West with a basement where illicit rum was hidden.


Little Room Jazz Club

821 Duval St, Key West, FL 33040
Phone: (305) 741-7515
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For a classy night out in Key West, visit the Little Room Jazz Club. Live jazz performances occur five nights a week.

The bar offers an elevated cocktail experience with signature cocktails, wine, and beer. The kitchen offers small plates of American comfort food.

It is a perfect place to have an intimate date night in Key West.


Sloppy Joe’s

201 Duval St, Key West, FL 33040
Phone: (305) 294-5717
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Sloppy Joe’s is a Key West institution. Try the pina colada with a heavy pour of dark rum. Sloppy Joe’s is also the home of the annual Hemingway Look-Alike contest, where thousands of hopefuls compete for that year’s “Papa.”

Be sure to order the original Sloppy Joe sandwich. The bar is a great place to visit for lunch or dinner.


The Bull

224 Duval St, Key West, FL 33040
Phone: (305) 296-4545
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The Bull is an open-air bar on the corner of Duval Street with local live musicians playing popular tunes for a crowd.

No one is a stranger at the bar; the bartender will extend a warm welcome and a cold beer, no matter what time of day or what you are wearing. Try the 2-for-1 margaritas from the daily specials menu!


Smallest Bar In Key West

124 Duval St, Key West, FL 33040
Phone: (305) 240-0860
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With just a few barstools, the Smallest Bar In Key West is a fun place to grab a quick drink as you travel down Duval Street.

Many famous faces have stopped by for a drink over the years. Check out the names on the barstools hanging over the bar!


Hank’s Hair of the Dog Saloon

409 Caroline St, Naval Air Station Key West, FL 33040
Phone: (305) 509-7758
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Hank’s Hair of the Dog Saloon offers excellent happy hours throughout the day and live music. Try the umami burger if you’re hungry.

My favorite cocktail is the Watermelon Cucumber Crush with Stoli Cucumber Vodka, lime, cucumber, and watermelon.


Tipsy Rooster Liquor Store & Bar

1325 Simonton St, Key West, FL 33040
Phone: (305) 295-5287
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The Tipsy Rooster Liquor Store & Bar is a 2022 Traveler’s Choice Award winner. Grab a cocktail at the bar and on the way out, stop by the liquor store for some reserves to enjoy later.

The bar has fantastic house-infused liquors!


Smokin’ Tuna Saloon

4 Charles Street, Duval St 200 Block, Key West, FL 33040
Phone: (305) 517-6350
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The Smokin’ Tuna Saloon is just off busy Duval Street; it is a fun place to have a cocktail to start or end the night.

Try the draft beer, Iguana Bait, brewed nearby–just up the highway in Islamorada. The frozen strawberry daiquiri is also a crowd favorite.


Flying Monkey

227 Duval St, Naval Air Station Key West, FL 33040
Phone: (305) 294-7525
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Check out the Flying Monkey’s vast frozen drink menu–the Banana Breese and the Pain in the Ass are two of the most popular.

Take home the souvenir cup with your tasty frozen concoction. Flying Monkey is located within walking distance of most Key West attractions on Duval Street.


Hog’s Breath Saloon

400 Front St, Key West, FL 33040
Phone: (305) 296-4222
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Always look for famous faces at the Hog’s Breath Saloon. Kenney Chesney has been known to swing by with his guitar for a set.

Try the Havana Hog Punch cocktail and a dozen fresh oysters while you enjoy the live music and lively atmosphere.


Lucy’s Retired Surfers Bar & Restaurant

221 Duval St, Key West, FL 33040
Phone: (305) 922-2616
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Lucy’s Retired Surfers Bar is known for its Infamous Scorpion Shot, where a real scorpion is added to a shot of alcohol. Those brave or foolish enough to try it can take home a free t-shirt.

For those who want a drink without extra protein, try the Flamingo Punch.


Durty Harry’s

202-208 Duval St, Naval Air Station Key West, FL 33040
Phone: (305) 296-5513
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Durty Harry’s offers live music nightly, so it is the perfect place to go when looking for an adventurous night out in Key West.

The bar offers straightforward cocktails and beer, but the dancing and singing crowd provides hours of entertainment.


El Meson De Pepe’s Restaurant & Bar

410 Wall St, Key West, FL 33040
Phone: (305) 295-2620
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El Meson De Pepe’s Restaurant & Bar is located in Mallory Square and offers delicious, authentic Cuban food.

What’s great is that as you head to Mallory Square to watch the acts and take in a breathtaking sunset, El Meson De Pepe has a sidebar selling incredible mojitos that you can sip while walking around the square.


The Waterfront Brewery

201 William St, Naval Air Station Key West, FL 33040
Phone: (305) 440-2270
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The Waterfront Brewery is a must-visit location in Key West for beer lovers. The bar has a happy hour daily between 4:00 pm and 6:00 pm.

Try the Blueberry Wheat or the Lazy Way IPA. You can also order a flight of beers to sample the most popular brews.


Final Thoughts

Key West is a vacation destination like no other, so no matter where you land, you’ll meet a friendly bartender and enjoy a refreshing beverage.

And if you’d like to explore more great spots in Key West, check out some of its fantastic sports bars.

Let us know in the comments below what’s your favorite bar in Key West.


Best Bars in Key West, Florida

  1. Green Parrot Bar
  2. Capt Tony’s Saloon
  3. Sunset Pier
  4. The Rum Bar
  5. Little Room Jazz Club
  6. Sloppy Joe’s
  7. The Bull
  8. Smallest Bar In Key West
  9. Hank’s Hair of the Dog Saloon
  10. Tipsy Rooster Liquor Store & Bar
  11. Smokin’ Tuna Saloon
  12. Flying Monkey
  13. Hog’s Breath Saloon
  14. Lucy’s Retired Surfers Bar & Restaurant
  15. Durty Harry’s
  16. El Meson De Pepe’s Restaurant & Bar
  17. The Waterfront Brewery

Paul Kushner

I have always had a deep interest in the restaurant and bar industry. My restaurant experience began in 1997 at the age of 14 as a bus boy. By the time I turned 17 I was serving tables, and by 19 I was bartending/bar managing 6-7 nights a week.

In 2012, after a decade and a half of learning all facets of the industry, I opened my first restaurant/bar. In 2015, a second location followed, the latter being featured on The Food Network’s Diners, Drive-Ins and Dives.

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