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.
For another dramatic sea view, the clifftop Aquinnah Shop Restaurant serves fresh seafood in a kitschy diner atmosphere, and the adjacent Gay Head Light is open seasonally for tours.
And speaking of famous faces, you may even catch a glimpse of President Barack Obama. Every summer the Obama family rents a property up island and frequents local restaurants and businesses.
Where to stay: The Beach Plum Inn & Food rates start at $195; beachpluminn.com.
The Outermost Inn rates start at $310; outermostinn.com.
In town, if you're looking for a mix of pretty much anything, Alley's General Store is the place to find it. Because it's the oldest operating retailer on the Vineyard, the vintage possibilities are endless. Grange Hall hosts an impressive farmers' market on Wednesdays and Saturdays, as well as community events throughout the year.
At State Road Restaurant, flanked by low stone walls and flower gardens, try a delicious fried green tomato BLT or savory field greens salad for lunch. If you make it in time for breakfast, the homemade granola is a heavenly way to start the day. Either way, pick up a chocolate bar to go. Made in house with ingredients such as caramelized almonds, pistachios, and espresso, the bars are named after towns and trails on the Vineyard, and are the sweetest finish at the end of a long weekend spent winding down up island.
Where to stay: Lambert's Cove Inn & Restaurant rates start at $100; lambertscoveinn.com.