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The lush storybook shores of the Leeward Islands have long been a natural playground for pirates, explorers, and sailors seeking rum, sun, and silver crescents of sand. This stunning string of islands includes some of the most popular Caribbean destinations. From honeymoon Antigua to sublime St. Kitts, you can spend weeks chartering around these super chic islands. Caught between the rolling surf of the Atlantic and the blue hues of the Caribbean, you can take your pick between hammock-swaying harmony, historic expeditions, or glorious adventures in the great outdoors.

When to go: November to July

Ideal itinerary: New Years in St. Barts

What not to miss: The archipelago offers many yachting choices. The 18 islands each have individual charms, with chic ports, modern cities, deserted beaches or tropical forests, there is an itinerary to suit any taste.