Caroline M. I'm familiar with most of these cities as well as the roads between them -- I did a road trip from Calgary to Vancouver a few summers ago and there are some fantastic things to do along the way. Send me a message and I'm happy to give you some pointers.
One thing you should consider is the weather and how that will affect the order of the cities you visit. While L.A., Vegas, and Austin may still be lovely in late December, New York and Boston will almost certainly be miserable and cold by then.
Cities I would add: Chicago, New Orleans, D.C., Philadelphia, both Portlands (Oregon has the bigger and more famous one, but Maine is home to the lobster-soaked original). And when you come to New York, make sure you spend some time in Brooklyn in addition to Manhattan!
Travel Forum 5 years ago