I have 4 weeks off beginning in late June and wanted to take the following trip (for approximately 2 weeks): leave from Rochester, NY, then travel through Nashville, Memphis, Austin, Santa Fe, Phoenix, San Diego, San Francisco, and end in Portland, Or. I've never done a road trip before, but I feel that this may be way too ambitious and won't give me enough time to actually stop and explore. For the way back, I am not sure whether it was best to drop off a rental car and fly back (and pay the high drop charge), or drive back a more direct route (i.e. through Chicago).
As I said before, I am new to this type of trip, so any suggestions are more than welcome.