Originally Posted by sailingfool
A stop in Scituate or Plymouth, then another in Cataumet...
I like the suggestion of Cataumet -- better than mine of Hyannis.
Plymouth/Duxbury is a great location too. However, I did not suggest it because it can take so long to sail up and into Plymouth Harbor (especially with a foul tide) -- almost as long as it takes to go the remaining distance to the canal. And then you have to double back on the way out.
But if you do go in there, you can save some time/distance by hooking a right at Duxbury Pier Light (aka "Bug Light") and anchor near Clark's Island (check charts carefully for depth at low tide). From there, if you have a dinghy you can go ashore on the backside of Saquish Head, which is a fun beach for kids (Clark's Island is private so no trespassing).
I have even seen boats spend the night anchored off the beach at Saquish Neck (between the Gurnet Light and Duxbury Pier) - but only with a fair forecast.