Is the trip to just "get you there" or is it a "Road trip!"?
If it is a road trip, I'd recommend first looking at places where you would like to stop. Schedule the trip as a trip, then come back and see if you have to make any changes due to charging.
Also, look at taking a different return trip. If you are going to spend time on the road, why not look at different things.
Also, you say "fall" so maybe you want to see some of fall. You may want to check out some of the fall color sites to see when each area is optimal. You may want to travel a little further south on the outbound and then a northern route on the way back.
If you are travelling for travelling. Check out the route suggested by Bing or Google maps first. See how close the Tesla route follows and where deviations may need to be made. Then look for charging support. The Tesla map only uses Superchargers, so it doesn't account for an overnight charge or even time it for mealtime charging.