Shelter Island, a short ferry ride from Greenport from the North or Sag Harbor from the South, this is a large island found between the North and South Forks of Long Island. This 12.1 sq. mile island is primarily residential with a few good restaurants, hotels and wonderful beaches. My favorites include:
Sunset Beach: This hotel and restaurant is a great spot on Shore Road with a 20 room hotel, French Bistro and great bar. It is across from the beach. This is the perfect spot for a drink at the end of the day to watch the sunset with a cocktail.
Vine St. Cafe: At 41 S. Ferry Rd., this is a great restaurant in the middle of the island under the same ownership as Blue Canoe in Greenport. The atmosphere is comfortable, yet contemporary and food excellent. I enjoyed the prix fixe menu before 6pm with some wonderful raw clams, a great miso glazed salmon on a bed of vegetables with rice plus a coconut sorbet for dessert. It is popular so make sure to book your reservation before.
The Chequit hotel gets good reviews as well.