The passage up the center of the channel looked relatively calm. I kept an eye out for other places where the waves broke as we neared the other side. A nice long section of spindrift appeared of a wave directly where I was considering going. So I didn't. There was an alternative.
Cuttyhunk harbor is protected from the south by an exposed sand bar with a breakwater at the end.
When I had looked at Ian's chart I had noticed the sand bar was quite narrow at some points. By heading south around the breakwater we had sheltered paddling up to the sandbar. I aimed for what appeared to be the lowest part and landed on a nice sand beach. Dave did a quick roll before landing to prove to himself that he could. We then carried the boats across the bar and paddled the rest of the way into the harbor.