.....My friend moved himself and his ship to Seattle and is flying me out to go sail this winter up the Canadian coast a bit ad maybe up to Alaska..... .
Well, you'll have no trouble finding an anchorage... won't be crowded.
I fear you're seriously underestimating the "cold" you're setting yourselves up for. Yes, you can equip yourselves for virtually arctic conditions, but generally those folks keep mostly dry.
Even above freezing can feel numbingly cold in humid, rainy conditions and you'll be guaranteed those. On top of that the north and central coast is pretty much steadily pummelled by sequential low pressure systems that provide high rainfall, gale force and worse winds on a regular basis. This is true pretty well from November through March.
As has been mentioned, hard it imagine a plan further from 'board shorts and flipflops'......
Reliable, safe cabin heat is a must.. a place/way to dry gear between travel days without creating a cold sauna below is another. Provisioning will be spotty outside of the few major centers along the way. Even fuel availability may be worse than during summer.
A boat and a boating skill set that can handle the extreme weather is yet another critical factor. Help will be relatively far away if problems are encountered.
Good luck with your plans.. it will be a memorable trip either way.. the challenge is to make it memorable for the right reasons.