TIPS for this type of trip:
1. When booking a hotel in a new city, locate it on Google Maps. Ensure that it is near the core of the city you plan to visit, so you can leave your car in the parking area of the hotel.
2. When visiting a new city, check out Wikitravel.org and put in the city name. It will tell you things to see and do; weather; facts; history...everything you might need!
3. No matter your interest, Google the topic for your city: public art walking tours in Pittsburgh OR museums of Pittsburgh, etc. Check out if any of it is free. Most cities have some free activities for tourists.