Sloppy Joe’s bar is a landmark on Key West’s Duval Street. (Photo: Russell Kord / Alamy)
Key West’s legendary drinking culture gained notoriety when Papa himself — Ernest Hemingway — frequented the island’s booze-filled bars. Today, Key West is known for its chill island atmosphere by day and raucous party scene by night. In fact, you’ll find some of the nation’s most iconic drinking establishments dotting the main drag, Duval Street. Grab a cup, and head out on a bar crawl of the island’s best spots to toss back a cold one.
Sloppy Joe’s has been a must-visit Key West establishment since it flung open its doors on Dec. 5, 1933 — the infamous day prohibition ended. It’s most famous patron was Ernest Hemingway, who allegedly gave the bar its name. Plan to hit Joe’s early — the bar opens at 9 a.m. — and stay to listen to live music at noon.
If you prefer to imbibe after dark, you’ll boogie down with more live music and dancing. Order one of the house drinks, like the Frozen Bacardi Light Runner, considered by Sloppy Joe’s to be “The Original Drink of the Florida Keys.” Bonus: Sloppy Joe’s hosts the annual Ernest Hemingway Look-aLike competition.
Conch Republic Seafood Company
Not only does the Conch Republic Seafood Company serve some of the freshest seafood in Key West, it boasts one of the island’s best views of the sparkling blue water and marina. The restaurant stands on the grounds of the former Singleton Fish House and Ice Plant, once the world’s largest producer of ice. For a signature Key West drink, belly up with a Bahama Mama or Jolly Rancher.
Rick’s & Durty Harry’s Entertainment Complex
Traveling in a group and can’t agree on where to grab drinks? Head to Rick’s & Durty Harry’s Entertainment Complex, comprised of eight bars in one building. Each bar has a different vibe ranging from low-key and upscale to rocking nightclub areas open until the wee hours. Check out descriptions of the different bars before you visit so you can find the location that best suits your interests.
If you’re feeling a more upscale vibe, check out 2 Cents restaurant and bar. With an extensive wine selection, 2 Cents is a great place to gather with friends and relax over a bottle of cabernet. Arrive hungry and stay to enjoy unique wine and food pairings, like a glass of Spanish Albariño served with an entrée of quail over white bean purée and herb pistou.
The Bull & Whistle Bar
Nope, you’re not seeing things after a few drinks. Technically three bars in one, The Bull & Whistle Bar let’s you experience very different atmospheres without leaving the building. The first floor, named the Bull, is the oldest open-air bar in Old Town Key West, a classic good-time dive.
Mosey up to Whistle Bar on the second floor to enjoy a quieter atmosphere and views of the area from the open-air patio. Finally, if you’re feeling adventurous, brave the rooftop Garden of Eden bar. Considered a clothing-optional bar, this nightclub features live music, dancing, and lots of flesh.
Make your way to Camille’s Restaurant, where staff and guests seem to know everyone who enters. Order one of the restaurant’s signature cocktails, like the Bacon Bloody Mary, and start off your day in Key West with a bang. Dishing out inexpensive, high-quality food like Mahi wraps and locally sourced shrimp cocktails, Camille’s is a favorite local’s hideaway.