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Step 1
Stroll through Oak Bluffs, the Vineyard’s somewhat honky-tonk center of bars and nightlife, and don’t miss the fairy-tale-like gingerbread cottages—tiny houses in bright pastels with lacy trim. Families with young children will also want to check out the Flying Horses Carousel, the oldest continuously operating merry-go-round in America (complete with brass rings).
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Step 2
Planning to imbibe? Bring your own beer or wine when lodging or dining outside Oak Bluffs or Edgartown. The other villages are chock-full of good shops and restaurants, but they are "dry towns"—no alcohol is served or sold. Luckily, most eateries allow patrons to bring their own.
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Step 3
For a spectacular sunset you won't soon forget, head to the cliffs of Aquinnah in the island’s southwest corner, where a lighthouse overlooks a high, unobstructed view of the Atlantic.
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Step 4
Enjoy the beaches, which are lovely (for a stroll, at the very least) even in winter. While some of the more popular stretches of sand lie on the eastern coast between Oak Bluffs and Edgartown, there are equally attractive swimming spots in the southeast and southwest corners, where a rambling trail leads down a hill to Moshup Beach. Though "Jaws" was filmed on the Vineyard, don't worry—true-life shark attacks are not a concern.
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Step 5
Be adventurous! Martha’s Vineyard visitors can take advantage of moped rentals, parasailing, horseback riding, fishing excursions, golf and more.
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Step 6
Shop till you drop: Edgartown offers upscale boutiques and galleries, Tisbury touts more down-to-earth shops, and Oak Bluffs is the perfect spot for souvenirs and kitschy keepsakes from the island.
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Step 7
Indulge in a little fine dining. Of course, seafood treats are a staple of the Vineyard, but you’ll be surprised at the diversity of top-notch cuisine; ask a local shopkeeper for tips.
