Dunno bout the cigars.. but when you hit Skagway, let me know if they still have the little kids down on the cruise ship docks passing out those stupid little newspapers.. I did that for about 5 summers!
We used to own a house up there, not anymore. Owned a few shops downtown on the boardwalk, but they've since been demolished. The Klondike Picture Emporium (Right next to the Kone Kompany) was owned by my uncle, not sure if it's still there either. Incidentally, if you want to pick up some jewelry of any sort for your wife, go the store called Heart of Broadway. It's owned by my aunt, and my grandparents work there. If you ask for Dewey or Carol Cosgrove, and tell 'em their grandson Nick sent you, they'll give you the best deal that they can.
If you've got time, definitely see the Days of '98 show, it's freaking hilarious!