I'm originally from "The Island" (Grew up in Northport). We live in Baltimore with our R31CB, but have cruised the LI sound several extensively. We plan to go back in two weeks. We are going to launch in Groton Conn, go to Block Island and then to the south shore of LI to a family party in Long Beach. You probably know this, but you can cut though LI via the Shinnecock Canal. It's a great way to get into the Great South Bay from LI Sound without going down the East River (although a cool trip) or around the South Fork and into the ocean. Great South Bay is amazing cruising with lots of gunk holing or marina hopping.
Where will you be keeping your boat?
Let me know if you want to chat.
Best,
Bobby