BF and I only have three weeks. Here is his plan:

Pennsylvania to Chicago
Chicago to Sioux Falls, SD
Sioux Falls to Rapid City, SD
Rapid City to Jackson, Wyoming
Jackson to Crescent City, CA
Crescent City to Reno, NV
Reno to Las Vegas
Vegas to Albuquerque, NM
Albuquerque to ROSWELL and then Pecos, TX
Pecos to San Antonia, TX
San Antonio to New Orleans
New Orleans to Atlanta
Atlanta to Charleston, SC
Charleston to Richmond, VA
Richmond back to Pennsylvania

I am worried that it is too much, but there's not much talking him out of that. Any changes you would make? More interesting things to see along the way?