Do you have good maps of the area the trip will cover? Most of what Buck asks you to tell him is marked on good maps. So check out some maps and see what it is that interests you along the way. Good maps also mark the scenic routes, which is what I look for when I want to stay off the interstates. If you don't have any, you should be able to get them all from CAA (free if you are a member). Or you may prefer a quality road atlas of north America.

When you have that, here is a paragraph to get you started:

Quote Originally Posted by AZBuck
Start with maps. Not GPS, not software, not Google, but real honest-to-god paper maps that show you your entire route, that you can mark up (and erase), that you can stick pins in, and that show something about the land you'll be driving through. Those are your essential tool in any RoadTrip planning process. Start by marking all the places you know you want to visit. Then connect the dots. Then look for more places of interest and scenic routes along the lines connecting the dots. Repeat until you've got as many sites and roads as you think you want.
Enjoy the planning.

Lifey