Sailing in the Caribbean breeze, over clear blue water, past lush green mountains… is there any image more representative of a vacation day in the Virgin Islands? Going on a sailing charter is a favorite activity during a St. John visit. The USVI are well known for sailing; the weather and scenery offer perfect conditions. Many captains have sailing stories from their Caribbean and world travels that entertain. Go sailing; delight in the wonderful weather, beautiful waters, and the service of professional and knowledgeable captains and crew members. Sailing charters are available in half day trips and full day. Amenities vary but very often include open bar, lunch, snorkel gear, floats, and other water toys. Sunset sails and dinner cruises are also an option. Enjoy the tranquil beauty of Caribbean evenings as the sun goes down and stars come out. Sitting on the deck of a sailboat watching the stars with a glass of wine is a lovely, romantic way to spend an evening. Visit the featured charters below for more information on what they offer!

Featured Sailing Charters

Contact Son of a Sailor Charters

Contact Sweet Pea Catamaran Charters

Contact Catania Yacht Charters

Contact Soulshine Charters


St. John offers rest, relaxation and an adequate amount of sporting activities. Plan the activities you would like to do most and have a great vacation!

Close Menu