I have cruised out of Peconic Bay for years and there is great weekend cruising. Shelter Island has three great harbors, Greenport, Sag harbor, ect.
But from New London it may be a long trip as there usually isn't any wind
Us Peconic Bay folk always called Long Island Sound, The Dead Sea.
We could always count on the ocean breeze to kick in around 2 oclock anyway. But get out beyond and there is nothing, so turn on the engine!
In 15 years I have sailed to Block Island twice.
what I call sail boats in the Summer is, Stick Boats. But it is fun no matter how you get there, and no matter where your going!!!!