Your 26 will be fine for the trip as most of it is in sheltered waters. Your hop to block and to buzzards through the canal will be your challenge but very doable.
I appreciate the need for short hops do to the kids. Forget Faulkner island in Guilford. It a restricted and no landing allowed. Consider stops on the CT river like Essex You then from there you can shoot across the sound to Greenport. (has a carousel for the kids) You can pick up a mooring at Jacks on shelter Island and take the ferry over to greenport. Spend the day swimming at Orient point harbor too. Leave greenport and swing over to sag harbor (bring your wallet). Plenty of anchoring and fairly well protected. Other choice would be three mile harbor. From there you can hit BI and from BI to Buzzards and on to the canal. Save Narragansett for the and Mystic for the trip back
I'll be heading up to Boston myself in July. My son lives there.
2007 Hunter 49