The 32 islands and cays of St. Vincent and the Grenadines offer the most varied cruising in the Caribbean. Find Barefoot Yacht Charters, the region's best outfitter, off the southern tip of St. Vincent. Their six-night, American Sailing Association–certified cruise school, aboard a 40-foot yacht, teaches guests to clear the anchor, trim the main, and laze on the beaches of Mayreau ($1,300; barefoot­yachts.com). Already skippered? Hire a sail from Barefoot and drift ($1,800 per week). Your destination: the 16-square-mile Tobago Cays Marine Park, home to a sand-bottom lagoon and six island playgrounds (tobagocays.com). Kick your feet up, bounce between islands, and tell your friend the hawksbill turtle you're never going home.