My cruising in LIS has been primarily on the Connecticut shore West to around Seabrook and the Long Island side as far as Orient Point. This summer coming we plan a cruise to New York City, staying on the LI side. The south and north forks as they call them of Long Island are very, very beautiful. There are a number of interesting and beautiful harbors starting at Lake Montauk headed west to Three Mile Harbor (abandoned house), then Sag, Shelter Island, Peconic Bay, and so forth. Moorings tend to be very, very expensive. Try $85/night but you can anchor many places except Greenport and maybe Deering Harbor on Shelter, but I'm not sure about that. Coming back east we usually stop at Mystic Seaport and Watch Hill. The sailing is usually very good along the LI shore as the southerly gets bent a bit more south so you can usually reach. However, late in the summer the wind is generally light in all of LIS.