Tom, the best way to do Cuttyhunk is to arrive late, anchor outside (I have a special spot if you email me) and then in the morning move to the inner harbor around 10:00 after you've seen a bunch of boats leave, and spend a whole nother day. It is one of the nicest places to go ashore and explore. Besides the climb up the hill, there are the oyster hatcheries in the ponds of the southwest side of the Island. Also, a friend mentioned that Gull Island off Cutty is now hosting a number of seals. He went out in his dinghy to watch them.