Many of the island’s beaches are private to the houses and communities dotting the shore, but there are still plenty of beaches open to all guests, including Owen Park Beach on the harbor of Vineyard Haven, Oak Bluffs Town Beach on Nantucket Sound and South Beach, Edgartown. Make a point to head west to Menemsha, where crowds gather to watch the sunset, applauding when it finally sinks into the ocean. Aquinnah, on the southwestern shore, is a great spot overlooking the Cliffs of Aquinnah, and the family can visit Gay Head Lighthouse before shopping in the Native American Reservation’s arts and crafts stores. John Adams commissioned the nation’s first lighthouse on this spot in 1799, but this red brick lighthouse didn’t make its appearance until 1856.