My husband and I are in our mid-50's and were 1st time cruisers. We decided to take a 4 day land tour prior to our 7 day cruise. Everything we did was booked thru Princess as we felt more secure that way. From the time we landed in Anchorage until we arrived at the Vancouver airport to depart, Princess handled our luggage and had it at our doorstep at each point along the way. This alone is amazing as they have several land tours that go in different (crossing) directions but all end up on the same cruise!
Our first 2 nights were at the Hotel Captain Cook in Anchorage. We are east coast residents and chose to fly in a day early to allow for the 4 hr time difference and to see some of Anchorage. The hotel was as expected from the various reviews I read. There are plenty of those so I won't go any farther with that. We took the Explore Anchorage tour which was $59/ea - not really worth it. I recommend taking the local trolley tour (ask the hotel desk) and also spending 3-4 hrs at the Anchorage Museum. This is a WONDERFUL museum with lots of history on the native people and the city of Anchorage. We ate at the Snow City Cafe and the Sandwich Deck for breakfasts - I would recommend either. Snow City is a bit more trendy while Sandwich Deck is basic breakfast food. OH, and while in Anchorage try the Alaskan Amber Ale - if you are a beer drinker, you'll enjoy this one!
Our 1st tour stop was Mt McKinley - very nice lodge, mountain was out in full view and everyone was friendly and helpful. A bonus to traveling in May is that you are the first customers of the season and everyone you meet is eager to please. Although some are new and the resorts just opened for the season so there were a few small hitches. But worth it to be welcome guests. Next on to Denali - a larger property but lovely all the same. The tour of the park that is included was nice and enough. Were lucky enough to see Dall sheep, caribou and moose in the park. We took the ATV excursion which for an additional $10 per person included dinner. You won't find food any cheaper!! The meal was pretty good too. Next day was a 9 hr train trip to the port of Whittier. It was on the double-decker train we've all see in brochures. The dining car was wonderful (if a bit pricey - captive audience!). Coming out of the tunnel and seeing the ship was a lovely site.
We were lucky enough to have our cabin upgraded at the last minute so we enjoy the additional space a great deal. We also had a balcony. Many said that would not be worth it in Alaska as it's cold in May. True, it was cold but totally worth it any way. We were able to view the glaciers on our balcony without being crowded and enjoy ALL of the views from inside our cabin thru the full glass door. I would be hard pressed to not have a balcony next time. They keep the ship spotless and the service was excellent. There were plenty of electrical plugs and hangers in our room although that may vary by room size. I did take a couple of those plastic hangers that bras come on and used them to hang a couple of things I hand washed so they were handy and small/light to pack.
1st port: Skagway. We took the White Pass Railroad (all day) trip. The Yukon scenery was worth it all! Lunch was pretty good and the town we stopped in (Carcross) was unique. Didn't get to see much of Skagway itself as the tour took up all of our time there. 2nd port: Juneau. We took the Northstar Trekking helicopter flight/hike to Mendenhall Glacier. WOW!! Very expensive but I would have passed on all other excursions and done this one if cost were a big concern. The young people who worked there were delightful and very helpful/accommodating. The flight was amazing as was the time on the glacier. 3rd port: Ketchikan. We took the Kart Adventure excursion here as my husband loves to drive fast. :) It was a bit scary for me (I just rode) but he loved it. I enjoyed the totems in Ketchikan and heard the trips to see them were good.
The weather was mid-50's. We did wear long underwear to the glacier and on the ATV and Kart rides. Otherwise 2 light layers under a coat were more than fine. It was mostly windy which made it feel colder. I had read all of the forums and reviews before so there wasn't anything that I felt surprised me. The formal nights had some in long dresses and tuxes and others in much less formal wear. So don't feel you have to go all out - pack what fits in the suitcase as you will only wear it once or twice.
All in all it was just as wonderful as we expected. Princess did a great job of getting us and our luggage where we needed to be. I'm glad we went in May. Many in AK said May was the best time to come - although, they may say that to everyone no matter when they come! HA! We did purchase and take a netbook computer to download our pictures on each day. That was a great decision as we enjoyed doing this and we didn't have to worry about extra digital cards, etc for the cameras. Plus when you are waiting at the airport or on the land tour, you can use the wi-fi.
I hope you enjoy your trip to Alaska as much as we did. Bon Voyage!!