Head "up island" to escape the crowds but still enjoy one of America's iconic islands.
If you're up for a walk or a bike ride, try the trail that climbs to the Quitsa Pond Lookout, where on a clear day you'll see not only Nashaquitsa and Menemsha ponds—dotted with shore-birds and sailboats—but also Vineyard Sound and the Elizabeth Islands two miles to the northeast.
Visit June through September to enjoy a little fresh-air retail therapy at the Chilmark Flea Market every Wednesday and Saturday in a grassy field on North Road. You're sure to see ceramics, artwork, jewelry, soaps, and antiques.
At the end of the day, the best spot on the island to watch the sun set over the water is the public beach at Menemsha Harbor. To complete the experience, pick up fried clams (to go) from The Back Door at the Home Port Restaurant. Or, for an iconic East Coast delicacy, head to Home Port or Larsen's Fish Market, which both sell lobster so fresh it might have been swimming earlier that morning.
Where to stay: The Menemsha Inn rates start at $195; menemshainn.com.