Insider's Guide to Martha's Vineyard

Head "up island" to escape the crowds but still enjoy one of America's iconic islands.

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Photo: Brooks Kraft


The beaches around the western end, such as public Moshup Beach, are as spectacularly colorful as the cliffs: Aqua water shines against yellow sand and lush green grass. Make sure you get great views of all that scenery—and plush comfort in your room, too—by staying at The Outermost Inn, but book early. The inn has only seven rooms and famous relatives (the owners are related to singer James Taylor), so you never know who might be in town.

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;

The Outermost Inn rates start at $310;

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