Fun in the sun and serious sailing make Antigua’s annual Sailing Week one of the globe’s premier watersports events. By day, skilled crews complete in more than a dozen different categories broken down by size and shape. By night, everyone parties like crazy in the island’s beachfront resorts and dockside pubs; sailingweek.com.
While you’re here: Visit Nelson’s Dockyard, the British Royal Navy’s major base in the Caribbean during the 18th and 19th centuries, and the one-time home of the distinguished admiral. Meticulously restored, the waterfront buildings are now part of the national park.
Where to stay: The über-chic Curtain Bluff resort spills down a Caribbean clifftop into a coconut grove beside the golden beach on the island’s south shore. Rates start at $715; curtainbluff.com.