remdog99,

I am no expert, but thought I would relay my experiance. Last April/May my first time to Italy, We rented a car at FCO (Rome Airport) and drove to Montisi a small town in Tuscany (home base for day tripping). The drive from Rome to Montisis was no problem. We took the "ring road" around Rome from FCO to the A1 autostrada north. We had a good map and kept Euro coins handy for all the tolls. From Montisis we took several day trips to Siena (good parking outside city walls)Florence (parked in Piazza Michaelangelo(SP) that was a minor headache but doable. Other day trips to Chuisi, no problem parked in town. Cortona, lots of parking lot options outside ancient city walls. All very doable. Here is a link I used for parking for Siena http://www.turismoverde.com/italia/info/parking.htm

I hope you have a great trip.