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Shelter Island, NY

Shelter Island is a place New Yorkers go to escape the madness of everyday life. Think of it like the Hamptons without the pretentiousness and crowding. Despite its populated surroundings, this beautiful, sleepy island somehow manages to transcend time, making old school souls feel right at home. From pristine beaches to luxe boarding, this place has it all. Just be willing and able to pay up for it.

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