As has been suggested Austin is a thriving music scene with several different kinds of music, alternative country, blues, folk, texas rock. Music there tends not to conform to labels. And the country side there is nice too (wear a hat) with some good places to go swimming.

At a greater distance, there is only one New Orleans. Music's home, where the street musicians are often as good as pricey headliners.

From Chicago go north to the great north woods in northern Michigan, Wisconsin, or Minnesota, and swim in the lakes.

Amtrak can be good or bad depending on traincar maintenence. The route through Colorado over the 'Rio Grande RR' route is wonderful. I'm in Northern California and the San Francisco Bay Area is still beautiful.