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Vieques Classic Charter: Our Story

Vieques Classic Charter was started by Captain Sebastian Watt in 2012 in response to the need for a more vintage feeling sailing charter in Vieques. The sailing charter started with the Shalamar, a boat with a colorful history and incredible lines, that was sadly taken by Hurricane Maria. In 2017, Vieques Classic Charter was acquired by the Livingston family and in 2018, Captain McCoy, family, and crew are incredibly proud to announce that a new vessel, Wind, will be replacing Shalamar as the primary vessel of the charter company. Vieques Classic Charter is one of the few classic sailing charters in Puerto Rico—offering sailing and snorkeling trips, Vieques sunset sailing charters, as well as many more “special” sails. Click HERE to learn more about our boat and our family.

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Four Hour Day Sail

A four hour day sail aboard a beautiful classic sailing boat; journey to a secluded reef on the eastern tip of Sun-Bay. First time boaters and expert captains alike, take the helm and perhaps learn something you didn’t know or always wanted to, as the emphasis is always on the sail and of course Wind. The Charter is from 11:00 am to 3:00pm and includes a snorkeling adventure, drinks, and a delicious lunch at a quiet anchorage. The cost is $150 per person or ask for private price.

Classy Sunset Sail

A casually fancy sunset sail complete with a gourmet cheese plate and cocktails along Vieques’ rugged coastline. Relax with a special someone and enjoy the view of Vieques’ historic Malecon from the majestic Caribbean Sea. Come, be enchanted by the sight of exotic seabirds whirling overhead, flying fish skipping across the bows, and the feel of our Wind. The charter starts at 4:00pm and the end time may vary depending on season. The cost is $150 per person or ask for private price

Trail and Sail

Start your day with Esperanza Riding Company on an incredible horseback ride cresting the foothills of Esperanza, winding through wooded arroyo’s, along Vieques’ own Playa Negra, and truly see Vieques how it was meant to be seen. Then to the sea, to continue your full day adventure with Captain McCoy, who will pick you up in a skiff to begin your afternoon sailing charter on board Wind–complete with brunch, cocktails, snorkeling and lunch. Charters last from 8:00am to 3:00pm. Please call for details.