I'm planning a solo road trip (though I have a couple friends that keep saying they want to join) as I have the last 2 weeks of August off. I live in Boston. I used to live in California, so I have done the whole PCH / Cali road trip. I've also done the Grand Canyon, Bryce Canyon, Las Vegas, Arizona/Sedona, and visited Nashville. Aka those locations aren't on my must-see list (but wouldn't avoid if they were on my route). I very much want to see more of the south... Austin Texas interests me, as well as New Orleans. I'd also love to see Savannah Georgia.
I'm having trouble making it all come together. I could fly out somewhere and rent a car, and make my way back to Boston. Or, I could start in Boston, rent a car, and fly back from wherever the farthest point is. I own a car, but doing a loop might be too time consuming for only two weeks.
My interests are not so much nightlife, but more sightseeing and touristy. I also am a sucker for cheesy roadside attractions.
I realize I'm all over the place here, sorry. Just looking for someone to give me some insipristion or insight. I've also never been to Chicago or Philly and would love to visit, but a) those aren't close to other locations and b) might be a good weekend trip with friends.