While there are many things to do in Key West, the city is perhaps best known as a place to party. Visitors looking to kick back with a cold cocktail are treated to a diverse array of watering holes from dive bars to swank hotel lounges. Even though craft beer and wine are growing in popularity, cocktail culture still reigns supreme in this resort town. Here’s a short list of some of the best spots in Key West to relax with a refreshing adult beverage.
Wasting Away in Margaritaville
Located in the old commercial waterfront area along Caroline Street, the historic and weathered Pepe’s Cafe and Steakhouse sports the authentic feel of an eatery that has really seen it all. Even though the margarita hadn’t even been invented when the restaurant first opened in 1909, Pepe’s tart fresh-squeezed version of the cocktail feels right at home in the shade of their covered brick patio paired with a plate of baked oysters. Tequila aficionados head to the newer Agave 308 Tequila Bar on Front Street for the posh establishment’s extensive list of premium tequilas and eclectic assortment of margaritas from the red pepper and cilantro to the starfruit and apricot.
Drinking Before Noon
While Rick’s is perhaps best known for its wild frat-party atmosphere, thumping dance floor, and spring break antics, tucked away on the ground floor of this extensive complex of eight bars is the more subdued Tree Bar. Eschewing pre-made mixes and offering views of the pandemonium along Duval Street, this small hangout has developed a hearty reputation for serving one of the best Bloody Mary’s in Key West. Over on Thomas Street, a converted former bordello and gambling den where Hemingway refereed boxing matches and patrons cheered on cockfights now functions as the cherished Blue Heaven restaurant. Wildly popular for breakfast and brunch, the restaurant specializes in tasty Mimosas and spicy Bloody Mary cocktails.
One of the smallest bars in Key West is the eight-seat Orchid Bar in the Orchid Key Inn. Using fresh ingredients, house-infused liquors, and premium spirits, the barkeeps craft a truly memorable assortment of cocktails. At the Ocean Key Resort and Spa, the hotel’s Sunset Pier and Hot Tin Roof restaurants mix up an impressive collection of classic Caribbean drinks. They also offer 90-minute interactive mixology classes during the week. A block away, the elegant ambiance of Bagatelle’s second-floor dining area is the perfect place to sip a gingery spiked lemonade or elderflower cucumber cooler while overlooking the bustling activity along Duval Street.
No trip to the Conch Republic would be complete without imbibing at least one rum drink. Sitting just 90 miles from Cuba, rum has long been the drink of choice for the island. Taking that affinity to the next level is The Rum Bar at the Speakeasy Inn. With more than 230 selections of rum, iconic Key West barman Bahama Bob Leonard mixes up some of the city’s most noteworthy cocktails.
Cocktails with Spectacle
If you are looking for things to do in Key West that feature local entertainment, La Te Da not only makes some of the city’s best Martinis and Mojitos, they also sport a piano bar festooned with original sketches by Picasso and a cabaret where Jose Marti once delivered fiery speeches in favor Cuban independence. For a more low-key experience, the Green Parrot is a salty dog institution catering to locals and featuring the best South Florida rock and jam bands.