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The 7 best bars in Key West

The best bars in Key West boats views as good as the expertly crafted cocktails

Megan duBois
Written by
Megan duBois

Key West offers its fair share of premixed cocktails like the classic rum runner and sweet frozen drinks that keep college kids on spring break coming back for more, but there's so much more to the island's cocktail game. True, it's taken a while for the tropical destination to get with the program, but now there are some incredible bars in Key West worth a walk or a ride on the trolley. 

While Old Town and Duval Street have some decent spots for people driving in from the mainland and being shuttled in from cruise ships, savvy cocktail connoisseurs know that even better drinks await on the side streets and inside some of the best restaurants where there’s plenty of rum, tequila, wine and craft beer to go around. So after you’ve had all you can take of Key West's beaches and to-do list head over to one of the bars on our list. It's pretty much always '5 o'clock on island time, and the bartender might just make you a cocktail worth bragging about back on the mainland. 

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Best bars in Key West

This Old Town stomping ground is actually the original location of Sloppy Joe's, and where Ernest Hemingway was often seen at a barstool until the late 1930s when he left Key West. For a bit of pirate lore, ask the bartender about the “hanging tree” that’s growing right through the middle of the bar. (Hint: It's where 19 pirates were put to death.) The dingy bar is also where Jimmy Buffet got his start. If you can’t decide what to order, get the Pirate Punch, the bar's signature drink.

If you absolutely must have a frozen drink while touring Key West go to Sunset Pier. The bar's location between Key West Harbor and Mallory Square means it has a great view of the water, so you can enjoy classic margaritas, daiquiris and mojitos as the sun sets. If you walk into the bar hungry, the menu offers island favorites like conch fritters and smoked fish dips. 


One of the most iconic bars in Key West is The Green Parrot, where the drinks are strong, the entertainment is a mixed bag, and locals and tourists are known to rub elbows. The bar was originally a grocery store but when war-time brought in sailors, the grocery store started slinging drinks ... and the rest is history. During the day, drinks and a juke box keep the atmosphere lively, but at night live bands and the once-a-month ukulele club bring a more upbeat island vibe.

Rum lovers will want to make their way to The Rum Bar at The Speakeasy Inn. The former Prohibition-era speakeasy is known for its knowledgeable bartenders and strong drinks. Belly up to the small bar to learn something new about the history of rum or what makes a good rum-based drink, while sipping on an expertly made pain killer or mojito from a bartender in a tropical shirt. Ah, paradise. 


This famous Key West bar originally opened December 5, 1933 but moved to its current location at the corner of Greene and Duval in 1937. The bar was frequented by Ernest Hemingway, and now Hemingway aficionados make pilgrimages to the bar for a taste of the author's past life. Most of the drinks are frozen concoctions, but it’s said that Hemingway usually ordered a Papa Dobles, a concoction made with rum, grapefruit juice, grenadine, sweet and sour, club soda, and a squeeze of fresh lime juice.

The oldest open air bar in Key West is The Bull and Whistle. Once inside, take a seat and admire the art that depicts the daily events of Duval Street. Downstairs at The Bull you’ll find lively entertainment from local artists, while upstairs at Whistle Bar you’ll get great views of the city from the al fresco porch. This is a great people watching bar, where the windows are always open – even in bad weather. 


Oysters and cocktails are a match made in Kewy West heaven. At Alonzo’s Oyster Bar diners will find a casual atmosphere and friendly service. From 4pm to 6pm the restaurant offers a daily happy hour where tapas and well drinks are cheap. If you’re looking for a drink with an island vibe check out the key lime colada, which turns key lime rum, piña colada mix, and lime juice into a perfectly tart drink served on the rocks.

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Most of the best Key West beaches are tucked away like hidden treasures. After all, this is not your typical beach town: the velvety-smooth sand dotting our man-made island has been imported from the Atlantic Ocean, the Gulf of Mexico and beyond and has to be occasionally replenished. 

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