With its endless shoreline and some of the clearest waters outside of Hawaii, St. Thomas was made for back-to-back beach days. If it’s your first time strapping on a snorkel, head to Secret Harbour. This small bay is the ideal wave-free spot to learn. Back on dry land, the capital city and cruise port Charlotte Amalie is packed with brightly coloured Danish colonial architecture—and pirate legend. (Keep an eye out for Blackbeard’s Castle.) Come April, there’s still good reason to visit, as the Annual Rolex Cup Regatta turns St. Thomas into a yacht-racing thunderdome. And the Carnival celebrations here, starting in the spring, are arguably the Virgin Islands’ best. Streets are overrun with sequins, feathers, and calypso music, even in the early morning hours, which locals call a “jump up” party.