Find the ultimate east coast relaxation on Shelter Island

I have fond childhood memories of sailing across the Long Island Sound from Connecticut and cruising into Shelter Island on a small boat to dock and dine. Almost 30 years later but the memories still strong, I returned to the island. This time I was reuniting with my friend Katy aboard the New London ferry as she wanted to introduce me to her childhood summer getaway once again and was eager to share how she was helping preserve and restore an arched white bridge from 1907 that managed to withstand the test of time.

The 27-square-mile island is literally sheltered (or sandwiched) between the north and south forks of Long Island – about two and a half hours (90 miles) east of New York City. Once the home of the Manhanset tribe of Indians, Shelter Island is now home to retirees and longtime locals and often caters to the uber-wealthy or those who have had family homes passed down for generations. It can only be reached by ferry from Greenport, N.Y. on the North Fork or North Haven, N.Y. on the South Fork.

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