I doubt that you will 'always be able t find a mooring or slip in late July to August' as this is the peak season for cruising. It is also in hurricane season so you might luck out.
That said, I bet that you can find places to stop along the way but it really is peak season at Block I. Others will chime in here I am sure.
Do you belong to a yacht club that has reciprocity with other clubs (some are better then others at this)?
If you want to keep your sails of shorter duration I would suggest staying in the Sound and visiting places like Faulkner Island and maybe some of the harbors on LI to avoid the MV/Nantucket/Block I. crowds. Even crossing the Sound from where you are in the usually light SW winds of summer could take 3 hours or more.
If you are 'done' with the Sound then just hop up the coast of CT to RI and make your way to Boston. Just be sure that any leg of your trip could be longer then 3 hours due to 'misunderestimation' of some kind.
I hope that others can give more hands on advice as we have no kids.
Sounds like fun anyway. Enjoy.
"The cure for anything is salt water~ sweat, tears, or the sea." ~Isak Denesen
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