You might consider wintering over in Prince Rupert, BC. Don't know what the visa issues for you might be in Canada, but PR
is no more than a week's cruise south of Juneau, so getting back to SE Alaska is not big deal.
The only thing I found difficult about entering Canada was that they were very strict on the quantity of adult beverages permitted. When I entered from Alaska I had just stocked up on wine and beer in Ketchitkan. I also had 8-10 bottles of rum in the bilge left over from the Caribbean. I was issued a "warning" and told to NEVER enter Canada again with so much booze on board. The discussion with customs on the booze issue took 20 minutes or so, whereas the discussion on the customs entry of the rifle (bear gun) I was carrying took 2 minutes. Go figure. In the post-9/11 environment I was pleased to see Canada had their priorities right.
Have a nice (long) voyage.