Above: Cliffs of Aquinnah on Martha’s Vineyard, Massachusetts

Few people visitMartha’s Vineyardjust once. It’s a place that captivates visitors the second they step foot on the island. Just an hour by ferry from Cape Cod, Massachusetts, Martha’s Vineyard feels delightfully isolated, and while it is tiny (roughly 100 square miles), you could spend years discovering its dirt roads, craggy coastline and calm inlets. Most of the island has no dress code: Jeans and sneakers will do in just about every situation. But as you drive around, you’ll also find sprawling waterfront estates with sweeping ocean views, fine restaurants and upscale boutiques. It’s this laid-back-meets-luxurious atmosphere that has captivated everyone from the Kennedys and the Obamas to James Taylor and Bill Murray.

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Above: Cliffs of Aquinnah on Martha’s Vineyard, Massachusetts