My husband and I cruised to Alaska the first time in very late September. We were the last boat up there, and had every port entirely to ourselves. But that was in the old days....1985. We did a 10-day round-trip from San Francisco on the Royal Princess when she was brand new. In our sailaway pictures, I am wearing a gauze summer dress, to give you an idea how warm it was. We had very good weather most of the way, with a little drizzle in Ketchikan. We visited Glacier Bay, and both agree that it was more thrilling then than it was on our recent cruise this year. Nevertheless, we enjoyed this summer's Alaska cruise on the Veendam more than the very sleepy one with Princess years ago. Maybe we were too young the first time to enjoy the longer sailing. Now it would be ideal to sail 10 days from San Francisco on a newer ship.
This year we were blessed with shirt-sleeve weather nearly throughout our entire southbound sailing the first week in August. But the most important thing to us was the ease with which we could lounge around on deck, with chairs everywhere, including wonderfully comfy ones on the Promenade deck, something Princess does not have.
And nowadays Princess has many more children on board and larger ships. We prefer smaller ships and far fewer children, so HAL met our needs much better, overall.
Nevertheless, Princess ships are very pretty, many are new and super-clean, and we like much of what Princess has to offer, and since there are a lot of activities to do inside with Princess if the weather should turn foul, that might be a good line to sail later in the season.
We haven't been to Skagway yet. Enjoy your cruise!