I would agree with Pilots point or
anchor at Duck Island. At the east end of the sound you might want to try Stonnington Harbor Dobsons marina easy in / out great places to dine and shop - Nappa tree/ watch hill is along way in and rough in a good blow. Fisher Island is also beautifully good anchorage great ice cream for the kids and the Pequot Inn for the older kids. I would do Stonnington easiest out to watch hill pass or Lords Pass.