Last year we took a cruise out of Whittier. We flew into Anchorage two days before the cruise to be sure we did not miss the ship and to see some things around Anchorage. We booked two hotel nights through Princess at the Captain Cook hotel that included a rail transfer to the ship the day of the cruise. Yes, we paid more for the hotel than we could have paid at other hotels, but for us it was worth having the security of the transfer. Not only was the train trip a pretty ride (Princess does also have a bus option) but you should be aware that going from Anchorage to Whittier is not like going to other ports. There is a one way tunnel on the way that the train and buses/autos go through and it is open and closed at various times. Also, we were able to book a tour from the Princess folks at the hotel for one afternoon pre cruise.