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The Five-Point Weekend Escape Plan

Turn Water Into Wine in Greenport

Beyond the vineyards, this North Fork town has a new, upscale hotel, secluded trails to hike and bike, and beaches to suit every preference.


1. Where to Stay

The view of Peconic Bay from one of the junior suites at the Harbor Front Inn.  

Be among the first guests at Cliffside Resort (from $375), a beachfront hotel opened July 4 weekend by East Hampton developer Ken Tedaldi. Cradled on bluffs overlooking the Long Island Sound, the 68 two-bedroom, two-bath suites come with wine refrigerators, balconies, on-site laundry, and access to a private beach. The Captain’s Roost, unit 207, has the best views of the sound.

The bright, contemporary Harbor Front Inn (from $299) is centrally located on the Peconic Bay beach and near downtown’s shops and restaurants. Book one of the oversize junior suites with a private balcony right on the bay, or splurge on the 800-square-foot terrace suite for the Jacuzzi tub, glassed-in shower, and a private patio with teak furniture.

Rent a cottage at the family-run, fifties-era Silversands Motel (from $300) and get an outdoor barbecue and picnic table on a quarter-mile stretch of private beachfront overlooking Shelter Island. Slips are available if you want to bring your boat.

Published on Jul 28, 2008 as a web exclusive.

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