New England charter itineraries usually start in Newport, Rhode Island, which was home to the America’s Cup for much of the 1900s. The city has a thriving waterfront of shops, restaurants and marinas that are wonderful to explore before casting off for a sail to Martha’s Vineyard and Nantucket. There, you will find the playgrounds of the rich and famous, who ride bicycles through the streets and attend clambakes on the shore.
Farther north, itineraries are available in Maine during the late-summer months. The scenery here is more rugged in beauty, with rocky trails to hike on any number of islands. Watch for traditionally elegant sailing and picnic boats here, especially in Southwest Harbor, the home of the storied Hinckley Yachts shipyard.