It looks like we'll be spending 7 full days on the road. We'll swing through lower Michigan and Churubusco, Indiana in order to see a few important people there, then everything else will be straightforward and without detours.
Day One: Cleveland to Chicago, 8.5 hours of driving
Day Two: Chicago to St. Cloud MN, 8.5 hours of driving
Day Three: St. Cloud MN to Brandon, MB, CANADA, 8.75 hours of driving
Day Four: Brandon MB to Saskatoon SK, 7.5 hours of driving
Day Five: Saskatoon SK to Grande Prairie AB, 12.5 hours of driving (OUCH)
Day Six: Grande Prairie AB to Fort Nelson BC, 7.5 hours of driving
Day Seven: Fort Nelson BC to Whitehorse YT, 13 hours of driving (OUCH)
Day Eight: Whitehorse YT to Skagway AK, 2.75 hours of driving/18.5 hours of ferry to Sitka!
This route was chosen to put us in big cities for the night whenever possible so that we'd have access to resources and less expensive hotels. It's a lot harder than the route that brought us to Cleveland, so we're going to have to rest up a lot and be very prepared. It'll be a huge adventure for all of us, and I can say that I'll be very glad to be doing this headed west, picking up a few 25-hour days that way!