An island city and Florida’s southernmost point, Key West’s history runs deep. It was inhabited by the Calusa people in pre-colonial times and became a Spanish territory in the 1500s.Just 90 miles from Cuba, this tropical fishing town is where one of Ernest Hemingway’s homes (turned into a museum after being auctioned following his death) is located and where he wrote many of his novels. He also drank quite a bit, frequenting bars like Sloppy Joe’s (open since 1933), which is still a hot spot for live music and debauchery 85 years later. Trending Now “Don't bother with churches, government buildings or city squares,” Hemingway said. “If you want to know about a culture, spend a night in its bars.” And so I did. Narrowing down my list was tough, but it’s a fun mix of oldies, goodies and newbies for an eclectic drinking experience that includes classic watering holes and craft cocktail experiences that’ll leave you yearning for an in-house mixologist.Built in the 1800s and still standing, Green Parrot Bar (another Hemingway fave), is the first and last bar on US1 as well as a Key West Historic Site. The vibe is friendly, drinks are cheap and you can catch live bands every night starting at 5:30 pm. When there’s not a band playing, feel free to choose your own tunes on the jukebox. Green Parrot even has free popcorn, for those of us who like a little something to munch on with our liquor.Right around the corner from the Green Parrot is First Flight Island Restaurant & Brewery. The building where it’s located was originally the birthplace of Pan American World Airways in 1927 and boasts garden canopy dining—think lush greenery and twinkling lights—and houses Southernmost Microbrewery, which offers wine, beer cocktails, house drafts and more.On the Roosevelt Ave. strip, Republica (just opened in April), is a lobby bar at 24 North Hotel and the place to go for a smoking rum cocktail with a hot date. Snuggle up on the couch and watch the bartender work his magic. The Cigar Old Fashioned comes in a cigar box, which opens to reveal a smoky concoction sure to please your nose, eyes and taste buds.Hop over to the more laid back outdoor bar just next door at the Gates Hotel. A poolside favorite here is the Rum Row Punch, a creamy and sweet blend of vanilla, passionfruit and mango rum with pineapple, cranberry and a dash of coconut milk.Also on Roosevelt, not too far from Old Town Key West, the Stoned Crab is a dockside restaurant at Ibis Bay Beach resort with fresh seafood and organic cocktails. The Eco Bar here is unique in that it uses only fresh, local farm fruits and sustainable liquors without preservatives. Order the Nutty Distiller here—a cocktail made with local key lime and coconut rums chilled and mixed with fresh coconut milk and served inside a coconut.Hidden inside an old historic mansion alongside a beer and wine bar, Caroline’s Other Side is dark, cozy and hosts a mix of tourists and locals. Like a lot of Key West bars, it seems to be a bit more local as it’s off the beaten path. Pay attention to the art; the best photograph, in my opinion, is a blown-up image of a sweet dog and cat each missing their left eye. Try the Adios Pantalones (or “goodbye, pants” in Spanish), a refreshing watermelon juice, Rittenhouse rye whiskey, coconut oolong tea and lemon juice cocktail served in a tall glass.At Key West First Legal Rum Distillery, tours are absolutely free (unlike at Papa’s Pilar Distillery, where tours are $10 per person and grant you $5 off a bottle of rum to go), and tastings are $10 and delicious. A sampling of six to eight different rums—including Chef’s Rum with real key lime, Chef’s Rum with green coconut, vanilla brulee rum and a spiced rum that tastes like Christmas—will definitely get you tipsy.The bartenders are chatty and well educated about what they’re serving, which makes the experience even more enjoyable if that’s possible. A stop here is 100 percent worth it and if you want to take a few bottles home, there are full-size options as well as a pack of mini bottles that are carry-on approved.In Old Town Key West, El Meson de Pepe is a family-owned and operated market, bar and restaurant that’s been serving up Cuban food and drinks for over 30 years. Catch the Sunset Celebration right next door at Mallory Square and then head to Pepe’s for tapas and a mojito. Pepe’s has a live salsa band, Caribe of Key West, that plays every day before sunset—the only local salsa band on the island.If you’re more of a beer drinker, there are breweries for you, too. Sampling local brews is always fun and at the Waterfront Brewery, one flight is just $8. Waterfront is open 365 days a year and is a restaurant and entertainment venue as well as a brewery (it’s just steps from a couple other places I love: Half Shell Raw Bar and the Cuban Coffee Queen).