The BVIs are packed with rookies, while the Caribbean's most southern islands, the Windwards, offer minimal land infrastructure and long, trickier crossings. Want a low-maintenance tropical sail that still delivers the rush of navigating open water? Head for St. Martin and the surrounding Leeward Islands, including Statia, St. Kitts, Nevis, and nearby Anguilla and St. Barts. Expect moderate, steady easterly trade winds, gentle currents, and water so transparent that spotting hazards is easy. Map a route from St. Martin, then charter a catamaran or hire one with a skipper from St. Martin–based Moorings. The beauty of this area is its mix of on-land activities (from remote bouldering to gourmet dining) and short-to-midrange crossings—meaning you can literally go where the wind takes you. On a two-week trip, you can snorkel off tiny Ile Fourche, eat steak frites on St. Barts, hike through cloudforests on Nevis, and sip three-dollar beers on St. Kitts' empty beaches. Charters from $650 per day; moorings.com
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