Note: All travel is subject to frequently-changing governmental restrictions—please check federal, state, and local advisories before scheduling trips.

Four hours by car from Miami, Key West—aka the southernmost city in the continental United States—is another world, full of colorful characters, history and a culture all its own, a place where almost anything goes. And what better way to immerse yourself in it than to spend some time at some of its finest local watering holes. Whether you’re parading up and down Duval Street, witnessing buskers entertain with comedic and, at times, daring feats as the sun sets in Mallory Square, or sipping libations from the deck of a catamaran while sailing from the harbor, there are plenty of memorable ways to raise a glass to this charming island city. Here are some of our favorites.

Best place to watch the sunset: Half Shell Raw Bar

For an island vibe just off the water, this harbor-side hangout can’t be beat. In 2022, Half Shell Raw Bar will celebrate its 50^th anniversary. Prior to opening in 1972, the building housed a shrimp warehouse in this once rough-and-tumble part of town. Today it’s an expansive bar and restaurant that smacks of Old Key West, decorated with patron-donated license plates (the first hung to cover a bullet hole—the result of an argument between two fishermen—to mark the shooter’s spot at the bar). Dine at wooden picnic tables on fresh seafood, including a wide array of oysters, served during lunch and dinner seven days a week, Don’t miss deals on seafood and half-off well liquors, house wine, and beer during the 4:30–6:30pm daily happy hour. Once you’ve finished your meal you can throw any remaining seafood morsels to the fish waiting in the water below.

Best place to people watch: The Bull & Whistle

There is no better place to people watch in Key West than on Duval Street, the main drag through town. Seek respite from the throngs of tourists and locals at the ideally situated Bull & Whistle on the corner of Duval and Caroline streets—three bars in one that serve all walks of life. On the first floor, The Bull is an open-air bar with a street side view of the action, accompanied by nightly live music. On the second floor, The Whistle offers pool tables, darts, pinball, foosball, and a wrap-around balcony on which to enjoy a warm breeze and the views below. Meanwhile, a DJ provides nightly music on the clothing optional rooftop bar, known as the Garden of Eden (camera, cell phone use, and lewd behavior prohibited).

Best place to hang out with locals: Virgilio’s

Also on Duval Street, but a bit more subdued in tempo and decor, Virgilio’s is a classic cocktail lounge, tucked behind La Trattoria Restaurant, which serves hearty Italian fare. Sip a selection of sublime martinis, like the Raspberry Chocolate Bomb, Caramel Apple and Pineapple Pizazz while enjoying live music and late night dancing. Opt to sit in the covered space or beneath the leaves of the giant tree growing in the center of the outdoor patio. Every Monday martinis are $7 during happy hour from 6pm until close.

Best place for a lively atmosphere: Sloppy Joe’s

Sloppy Joe’s Bar, Key West, Florida

Sloppy Joe’s is a must on every visitor’s list, with a long history serving those stopping in Key West. The bar opened on December 5, 1933 a block down the road, moving on May 5, 1937—patrons, seats and all—to its current location, when owner Joe Russell learned the rent would be raised a dollar. Hemingway frequented the place, and encouraged the name Sloppy Joe’s after another of his favorite watering holes, the Jose Garcia Havana Club in Cuba. Sloppy Joe’s is open for lunch and dinner daily, with live music during three sets throughout the day—switching from guitar to a nightclub vibe later in the evening. Tourists flock to this crowded spot to dine on bar fare including Sloppy Joe nachos and sip libations like Sloppy Ritas (the house margarita) amid Hemingway memorabilia and flags donated by customers from all over the world. The bar even hosts a Hemingway lookalike contest annually in July, with pictures of former contestants on the wall. Shop for souvenir merchandise in the adjacent store.

Best place for live music: The Green Parrot

Green Parrot Bar, Key West, Florida

They say sooner or later everyone winds up at the Green Parrot and it’s no wonder, as its known for an eclectic mix of live music offerings, including “soundcheck” sets Friday–Sunday from 5:30–7pm, allowing an early bird crowd to experience the same talent at a reasonable time of night. In addition to live music, a 100-CD vintage Rowe jukebox fuels the interests of every manner of music enthusiast. The building dates back to 1890, first as a grocery store and then as a bar since WWII, catering to the navy customers from a submarine base down the street. When the navy closed the base in the ’70s (only to reopen it several years later) the place was renovated and became a hippy bar until it was sold in 1983. Friendly, no nonsense bartenders serve a mix of locals and tourists from 10am–4am in an expansive space, void of frills but adorned with colorful, donated artwork. Past celebrity clientele includes John Goodman, Michael Keaton, and Jamie Lee Curtis.

Best bar with outside seating: Smokin’ Tuna Saloon

Join the lively crowd of visitors and locals at this popular hangout, boasting several sets of live music seven days a week, performed on the courtyard stage. Enjoy a full menu of fresh seafood, including a raw bar serving up more than 90 “personalities” of oysters. Wash them down with tasty libations such as a Cucumber Mint Cooler or a Smokin’ Dirty Banana. The Mercantile opens at noon, while the bar and restaurant open at 2pm. Smokin’ Tuna is home to the annual Key West Songwriters’ Festival, held in May and drawing big name talent—the largest festival of its kind in the world and the largest country music festival outside of Nashville.

Best bar with a colorful history: Captain Tony’s Saloon

Captain Tony’s is such a signature spot, and arguably the oldest bar in Key West, that it’s been featured in several Jimmy Buffet songs. Along with Buffet (who got his start here), Hemingway, Truman Capote, Tennessee Williams, and Shel Silverstein frequented this saloon–a casual dive bar owned by the late Tony Tarracino. The larger-than-life owner’s storied life included work as a shrimper, fishing boat captain, gunrunner, casino operator, and mayor of Key West. The building was built in 1851 as an icehouse that doubled as the city morgue, housed a telegraph station in the 1890s, a cigar factory in 1912, and later a bordello, before becoming the site of the original Sloppy Joe’s Bar from 1933 to 1937. The 428 Greene Street location remained a bar, purchased by Captain Tony in 1958. The ceiling is covered with donated ladies’ bras while business cards plaster the posts around the bar framed by stools painted with the names of famous patrons. A “hanging tree” grows in the middle of the place, where 17 people were once hanged, which may explain why many say it’s haunted. Captain Tony’s jewfish still hangs above the door. Come here for live music, pool, and cold beer.