I think most those "reality" shows, are in it for the drama, but who wants to watch a truck drive 1000 mile round trips, endlessly, year round.
TSB, grab your camper or trailer, buy some fuel, make a trip of it, to enjoy this you need to like driving and should have six weeks or so once you get to Canada, I would plan eight weeks if retired.
You can put your wheels on the boat in Anchorage Alaska to Tacoma Washington but then you need to fly that streach. http://www.totemocean.com/vehicles
Or you could take the Alsak state Ferry up the coast from Washington and then drive around Alaska and then down though Canada, tell your wife you are going on a Cruse.