Top Ten Caribbean Classic Adventures

You'll find plenty of chances to sail in the Caribbean, but the most unique locale is found on the south side of Sint Maarten. No other Caribbean destination gives you the chance to actually crew and race an America's Cup yacht—including the Stars and Stripes, the winner of the 1987 America's Cup. The 12-Metre Challenge is offered daily from Bobby's Marina in Philipsburg. Best of all, you don't even have to know port from starboard to become one of the crew. Each guest is encouraged (but not required) to learn and perform one of the many tasks in sailing these greyhounds of the sea. You might be operating the hydraulic primer to control the boom and keep the sails tight, working as a backstay grinder or trimmer to move sails and ropes, or powering the mighty Genoa sail as a primary grinder. The 12-Meter Challenge costs about $70 per person.