Cruising Long Island Sound
I wud consider getting a little more creative with your plan. Personally, I would hump it, with or without your kids, to get out of the western sound where, in the summer, the winds can be quite light. If you are willing to extend your range, Newport is a great destination as is Block Island and even Shelter Island. Maybe consider an early morning start or an overnight to keep the kids happy. Brewer Marinas are typically excellent in terms of being kid-friendly and amenitities. I have kept my boat at Pilot''s Point in the Past.