Low-key and relaxed, Mo-Bay (as the locals call it) is warm year-round. Swim and snorkel in clear water at Doctor's Cave and Fletcher Beach, dive in the ominously named Widowmaker's Cave, golf on courses such as Half Moon and Tryall. Off the beaten path, feed a hummingbird at the Rocklands Bird Sanctuary and tour Rose Hall Great House, a former sugar plantation with a spooky past. After dark, feast on jerk chicken, dance to a reggae beat and gamble on Gloucester Avenue, a.k.a. the Hip Strip.
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