I would like to rent a car outside of Rome and see Siena, then Pisa ending up in Florence in one day. I know I cant park in Siena, but would like to have a little taste of the driving experience in my short time in Italy. I don't plan on spending very much time in Pisa, but my daughter wants to see the tower. So if I have a full day for this route(spending most of my day in Siena) and end up even in the evening in Florence is it doable? What would be the best roads to take? I will return the car in Florence and then spend a few days there and then train to Venice.
I wouldn't use a car to go to Pisa. It's much faster as a half day trip from Florence by train. (1 hr each way+10 min bus to the tower+5 min to see the tower and take 2 pictures while pretending to hold it up). Leave after lunch and return by dinner. Siena is an easy day trip from Florence by bus or train (bus is faster). 75 min each way. If you want to rent a car to test your driving skills in Italy you have 2 better choices: 1. Rent in Rome or Orvieto then drive to Florence through the Tuscan small towns using the regular roads. Look at the map and decide which small towns you want to visit. One day only however will give you little chance to see too many places. Montepulciano, Pienza, Montalcino are some choices. 2. Go to Florence, find a hotel near via Borgognissanti (all rental car companies are there), rent the car for a day and take a drive through the Chianti road to Siena, then drive back up through the via Cassia or the freeway, stopping in Monteriggioni, San Gimignano, and maybe Colle Val d'Elsa.