Take advantage of the island’s bike-friendly terrain, Mashomack Nature Preserve, Kayak Tours and pristine beaches. Take part in a Shelter Island tradition on the front lawn of the Pridwin at their Wednesday night barbecues ($35 for adults, $19 for children), where you can chow down on all-you-can-eat items like grilled shrimp, clams, steak, hamburgers, hot dogs, and corn on the cob, while listening to live music and chatting with local islanders. There are plenty of beautiful beaches on Shelter Island, and is close to the Hamptons and Greenport which has a lot of action going on there as well. There are 2 ferries to get to/from the island. One takes you to Sag Harbor/The Hamptons, and the other ferry takes you to Greenport.