Love Alaska!
The Alaska board helped us plan a fantastic trip, both land and cruise. Lots of info re tours, etc
https://boards.cruisecritic.com/forum/33-alaska/
One of our best vacations ever!
Agree with sweatshirts and windbreaker for SF and first and last few days.
You will also need if going to Volcanos National Park. Altitude and wind make it brisk even if sunny and warm at shore.
October in Salem is very crowded, lots of traffic, etc. It is not that close to Boston (45- 60 min, no traffic) so would imagine that may be why Princess doesn't offer tours there.
We had a lovely UBD on late evening departure from Curacao on a Circle Carribean this March. Since ship didn't leave till after 9pm, we were able to enjoy dinner without fear of windy conditions.
Hope that might be an option for you.
Live Chat was a big help to get Medallion app completed.
After numerous attempts on various media, I tried Live Chat and was quickly provided a link that worked with booking number.
Not a problem last fall, this was so frustrating for March 3 cruise.
Finally Resolved by best CS person ever!!
Betty at Princess CS, immediately noticed it was a hold and removed without penalty etc.
We had spent a good bit of time yesterday with various CS reps who could not figure this out.
Many thanks to all.