Haven't sailed Puget Sound but I've chartered in the San Juans a number of times. I have always used San Juan Sailing in Bellingham and they've always been great. May,June or Sept. are good months. The kids are still in school so the crowds aren't nearly as large. The winds will probably be better than July and August and everything will be open.Taking two weeks and including a swing into Puget Sound would be a great holiday. It's hard to beat the Pacific Northwest.