Summer is Coming!
This is definitely on my to do list. My to do soon list.
It's not for inexperienced paddlers, but what I love about it is all the permutations. From the head of the Cape Cod Canal you can get to four or five inns or b&b's in less than ten miles of paddling.
I haven't done this trip yet, except for the loop from Woods Hole out to the Cuttyhunk Bass Club and back. (I didn't stay at the club, but with a friend on the island...) But it's part of a larger plan to finish circumnavigating the entirety of Cape Cod. I've done from Massachusetts: Inn to Inn Along Cape Cod, and from Provincetown down to Wellfleet. So though this gets a bit sidetracked--I'm going around the bay rather than through the Cape Cod Canal--it's part of a piece.
The only downside about this trip, and sea kayaing inn to inn trips in general, is how much the weather can play with your plans. So flexibility is the key. Even in the relatively sheltered waters of Buzzards Bay, if the wrong wind kicks up you could be in for a hell of a push. Or, if your smart, a lay in day....