Oak Bluffs, Martha's Vineyard
How to get there: Hop aboard the Seastreak catamaran to MV for panoramic views of Manhattan, Roosevelt Island, Queensboro Bridge, the Long Island Sound, and Block Island. Ferries operate every Friday from May 25 through Labor Day. Prices are hefty, at $240 round-trip.
This quaint, if slightly touristy, town is full of adorable, Candy Land-esque "gingerbread" cottages for your ogling pleasure, plus numerous public beaches perfect for fishing, boating, or lounging. The best spots to visit include tasty seafood restaurants, inviting watering holes, and shops peddling preppy duds. Fudge shops and bakeries only sweeten the deal.
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