"No trip to the Caribbean is complete without swigging some rum, but the Keys has plenty of the golden stuff on hand as well. The hip Gates Hotel in Key West is home to Rum Row, a hopping bar next to the L-shaped swimming pool. Through an exclusive partnership with Key West’s own First Legal Rum Distillery, the bar slings cocktails like the Up in Smoke, made with aged Key West Raw and Unfiltered Rum, mezcal, ginger, and lime juice. To partake in a scene with an even stronger pirate vibe, head to the hotel’s cigar lounge." - Devorah Lev-Tov