The Caribbean islands are bursting with adventurous activities, pristine beaches, and stunning natural sites; the best way to explore them is, naturally, by water. For the sailing journey of a lifetime, join the Class America sailing race on the America’s Cup to the Dominican Republic. Enjoy some deep sea and offshore fishing as well as wrestle a shark on a private Island. The Caribbean offers the perfect backdrop and sailing conditions with their warm and steady trade winds and picture perfect surroundings. Whether you're a novice or trained sailor, embarking on a sailing vacation is one of the most revitalizing and uniquely refreshing adventures ever.