Go East my boy, go East
Although LIS is a great cruising area, winds tend to be light in the summer months and also predominately from the SW. Which means going West you will be motoring quite frequently if you want to get anywhere! Once out of the Sound, the water is cleaner, and the breezes fresher. As the other folks mentioned, Block Island is great, Shelter Island, Newport, Cuttyhunk, the Vineyard. You can't go wrong with any of these places. But,if you are planning on dock space at some of the more popular spots like Newport and the Vineyard, call early for reservations. They sometimes are booked early in the season. Also, get yourself a good cruising guide...I use Embassy guides and really like them. They have several, so make sure you get the one that covers the area you will be cruising. "So many places to go, and so little time". COME ON SPRING