- Challenge yourself to some open-water sailing in Block Island and Long Island Sounds. One day of cruising will take you out into Block Island sound, and then into Long Island Sound. Your choice of destinations within a day’s reach is limitless. Cruise on to Block Island, Montauk or Sag Harbor. Take your time in Long Island Sound and cruise around Plumb Island, Gardiner’s Island, Shelter Island and/or Fisher’s Island. If the Hamptons are your final destination, cruise around Montauk and head west to the Shinnecock Inlet.