For 10 years or so, my wife and I boated through the San Juan islands, just north of Seattle -- up into Canada.
Our favorite time of year was winter. Rain & mist only made the islands look prettier. The weather kept away the martini/party crowd. Easy to get slips at marinas. Quiet. The boaters who were out were more experienced and thoughtful. Didn't use the boat nearly as much during the summer. The PNW was a good fit.