Driving in Tuscany, etc.

I'll answer the easy ones. In addition to your Virginia driver's licenses, each driver must have an International Driver's Permit. You get this at a AAA office here in the US (you don't have to be a member) and it costs $15 and is good for a year. It requires photos, but some have said that you can get the photos at the AAA office for free or at low cost - check how your closest office does it. You must learn about ZTL's, areas in and near the centers of cities where cars are not permitted. These are enforced by cameras, and heavy fines will come your way months after your trip if you enter one (even inadvertently, and even a little bit). Furthermore, the fine is for EACH infraction, so if you get confused or lost, it's easy to rack up 3 fines in 10 minutes. In addition to the fine itself, you will pay another high fee to your rental car company for passing on info about your car to the police. Florence's ZTL's are the most notorious, but more and more cities have them. Florence has become so bad that the usual advice is to take a bus or taxi to the airport and rent there, where you can avoid the ZTL's easily. Towns with ZTL's usually have parking lots outside the forbidden zone, where you can leave your car and walk or bus in.

Marjie, in Siena there are public lots but some of the larger hotels near the city gates may offer parking; Hotel Minerva has a covered garage on the property, and some of the rooms have views of the city skyline - it's very close to the city gate, you can take a bus or walk in. If you plan to daytrip, there is a bus connection into town from the public lots. In Assisi, there are also public lots at both ends of the town, but when I was there a couple of years ago we were able to park for free at the foot of the Rocca Maggiore (the old castle at the top of the town), and then walked down to our hotel in the center of the city. The bus doesn't go all the way to the castle, as I recall, but there is a series of staircases from any part of the center of town.

Driving in Tuscany is very easy, just make sure you have a GOOD map, or garmin. Here is a list of the individual wine roads. we have don a few of them.
http://www.in-tuscany.com/wine-road/

For the International Drovers Permit, my local AAA office charges $10 for the photo, making the total cost $25. You can bring in your own passport sized photo if you wish. For $10 I choose to take care of everything in one place. The IDP is good for a year and each driver will need one.

If you are doing the obligatory stop to Pisa, you might enjoy drive 30 minutes to the town of Lucca. You'll know you are there when you see you are driving along a huge wall. Park and walk in. Then you can rent a bike (for one, two or a family) and bike the 3km length of the wall. It can take an hour or the whole day if you get lost in the joy of it all!

Fantastic, driving in Tuscany is the best way to see it. Do NOT drive in Florence, I tried that twice, slow learner! Yes, parking lots are easy to find and use. Sienna, Assisi both have easy lots. Pisa maybe not. Towns to see. San Gimignano, Pienza, Lucca, Volterra, Perugia (Umbria), Montecattini Alto, Portovenere, Monteriggioni. Wine: Montalcino, Montepulciano. Driving to 5 Terre is hard. You can get to Monterosso al Mare but it isn't easy and it takes a long time. Train from La Spezia is better, you can park there. Portofino is just a ways north. Have fun!