You do not want a car if you are staying in _______ Italy. Fill in the blank of any city over 400,000.
Train service is great. The small towns are great. You can find where you can stay and park from red Michelin guides.
Rada in Chianti has parking and you really need a car there.
Gatanara has parking, and you really need a car there.
Two weeks is enough time to go 2 or 3 major places.
If you are into art and history and the like, go to Rome, Florence and Venice.
If into wine, go to Montalcino, Rada, Piedmont.