To really see Italy, the best way is to rent a car. You get to see so much more of Italy that you wouldn’t otherwise see. The driving isn’t that bad once you get used to it. You just need to pick up the rhythm and you will fit right in.
PS – make sure you go to Italy with an International Driving License – you can get at any at AAA. It is good for 12 months.
I was staying in a villa near Cotona in the Tuscany region with 4 adults friends, thought we’d rent a car when we arrive in Rome and see Pisa and spend a couple of nights in Rome and do a little touring in the Tuscany region mostly. I have driven through Holland down to Paris without any worries. In the Tuscany countryside region & other areas, it can be a beautiful experience to drive. Especially when you are in a villa & want to come & go as you like, you will have the flexibility for going out at night.
Drive – yep, you certainly should do it. It is the only way to discover the out of the way places. Train travel around the country is great but to have a car to make your way though the Italian countryside will make for a memorable trip.
Don’t forget to buckle up!
However, in cities such as Rome or Pisa you will not at all need a car. In that city you will pay higher fees for parking. The thing about every Italian city is that they are walking cities with excellent train & bus systems. Renting a car in Italy can be incredibly expensive! Also the rental company might not let you travel into Rome itself.
I would take the train from Rome to Pisa or vice versa, then pick up a car back in Tuscany in either Pisa -close to Florence/Tuscany, or train to Florence/Sienna & pick up the car. While in Tuscany you will also be going to Florence & you will not need a car for that city as well.