great plans, we almost always fly to places, doing it your way is much more relaxing. You won't have a person putting the seat back into your lap, you won't have the dinging of the fasten seat belt every couple minutes. You will have the ability to stop and get an actual feel of the places you pass instead of seeing them through the clouds. Maybe you can see Martin Milner in that '62 Vette along the way!
Bring some "Travlin' " music I'm sure...Van Morrison may have a sound slot....Maybe some George Benson.....just a couple of ideas there....Get a tattoo of "Route 66" at some place along the way to finish it out! Put it in a prominent place, maybe your back calf, or your upper thigh....LOL....