Named for the 18th-century pirate John ‘Calico Jack’ Rackham — the man who sailed with the legendary Anne Bonny and Mary Read, and whose downfall reportedly came when his crew was too drunk to fight the authorities who eventually caught them — Calico Jack’s on Runaway Bay leans into the pirate legacy with the same energy the original Calico Jack brought to, well, everything except that last battle. Situated on Half Moon Beach with five-dollar round-trip boat access from the shore, this island bar offers panoramic Caribbean views, strong cocktails, and a grilled lobster situation that deserves its own legend. The reef system nearby is excellent for snorkeling. The sunsets are dramatic. The drinks are named for people who probably would have appreciated them. It’s one of those Jamaican gems where the history makes the rum taste better.
