Wonderful article Megan!  Years ago we took advantage of a very late season cruise from Seward to Vancouver through Southeast.  I had lived from Annette to Gustavus over the years so was familiar with a lot of the stops and cities.  But others I had never been too and Skagway was one.  Past it many times but never there.  We marveled at the three cruise ships that appeared and disappeared within hours but really enjoyed the history of the place in a way you can only experience by being there.  So yes, there is this head scratching dichotomy but as you write, it works.