Sample Itinerary – 7 days
Day One: Arrive in Newport, RI and board yacht. After getting settled, enjoy lunch underway to Cuttyhunk, a part of the Elizabeth Island chain. There will be plenty of time before dinner to explore this quaint fishing village on an island with a year round population of fewer than 200 people.
Day Two: After breakfast depart to Vineyard Haven on Martha?s Vineyard. After lunch on board you may choose to hire a car and explore the exclusive village of Edgartown, take the tender to Oak Bluffs, or simply bask in the sun on the beach where the film Jaws was filmed.
Day Three: After breakfast cruise to historic Nantucket Island. This is a location that deserves at least two days with its world-renowned restaurants, shopping and beaches. If you are planning any meals ashore this is the place to do it.
Day Four: Layover in Nantucket.
Day Five: After breakfast, chart a course for Provincetown, an eclectic resort on the tip of Cape Cod. One could spend an entire day here just admiring the many examples of architecture in this truly artistic community.
Day Six: After breakfast head for Marblehead, a harbor steeped in New England Yachting tradition. A walk through the town is the equivalent of a garden tour as there seems to be a summer long competition among the locals for the most extravagant flower boxes.
Day Seven: After breakfast make the short hop to Boston for a visit to Rowe?s Wharf at the head of the harbor and just across the street from Fauteuil Hall. The sky is the limit here and a shopping tour of Newbury Street is highly recommended.
(Thanks to International Yacht Collection for the above itinerary):