A friend of my son went up as far north as Glacier Bay a few years back in a boat about your size. They left in April. I'll see if I can find a link to his blog. Can't give you any advice on sailing in rough stuff. I"ve been boating in the Puget Sound for 25 years and try and stay off the water if there are gale warnings. I didn't know we could get 14' swells in the San Juans. That must have been kind of scary
1983 Fraser 41
La Conner, WA
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Boating for over 25 years, some of them successfully.