Start with a trip planning software. We use Microsoft Streets and Trips. Input the major locations you want to visit. Set your preferences as to how long you want to drive each day.
Order Tourism guides for each state or province which you are going through. Go through each book when they arrive and look at your specific types of activities. Let your traveling partner do the same thing. Yes, there is a lot of advertising, but there is a lot of good ideas. Add any specific points to the route and see how it works.
It may take some adjustments.