Our first trip to Skagway was in the late 70's when our family did a 5 day backpacking trip on the Chilkoot Trail. We have been back in more recent years and it has changed dramatically now that the cruise ships come in. It is still a quaint place to visit.
Something else that is fun to do is the narrow gauge train trip from Skagway north to Bennett. They stopped running it for many years, but I think it is running again. Lunch was served in the old Bennett Train Station (a sight we were happy to see at the end of our backpacking trip).