The 7 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.