With consistent breeze, gorgeous beaches, incredible islands, great yachts and first-class charter service, you’re sure to enjoy cruising the New England waters. Your sailing charter adventure starts in the most famous harbor in New England, Newport, Rhode Island. If you love sailing and have a passion for new and exciting experiences, then the Newport sailing area is your perfect choice to start your sailing adventure.
Sail out of Newport and head West towards Block Island, Montauk, Fort Pond Bay, Fisher’s Island, Greenport, Shelter Island, Sunset Beach, Sag Harbor, New York, or Mystic, Connecticut. To the East, are the world-famous destinations of Martha’s Vineyard, Cuttyhunk, Nantucket, Padanaram, Menemsha, Oak Bluffs, Westport, Elizabeth Islands, Hyannis, Cape Cod or Boston, Massachusetts.
The Waypoints Annapolis® Newport charter affiliate is home to the largest, most modern fleet of sailing yachts in New England. By maintaining our yachts to the highest standards, we ensure that you make the most of your time on the water and enjoy your sailing vacation.