It appears that in order to see several villages we will have to break down and drive for a period of time while we are in Italy. Since we've never done this before, what guidelines can you provide? Thanks in advance!
You probably need a car in Tuscany. Or hire a driver. You can get to some of the towns by bus and train like Siena but others you will need a car for.
You need an IDP, which you get at AAA. I can’t think of any other guideline you need. If you can drive at home, you can drive in Italy. Read up on ZTL so you know how to park and you’re all set!
We've driven in Italy on a number of trips, without problem. Generally speaking, in Italy (and I think in Europe generally), signage more often provides the names of cities / towns, instead of road numbers. Navigating by names of towns is easier for me.
Off the highways, roads tend to be narrower than in the U.S., and with smaller shoulders (probably also the case in some places in the U.S.). Like everywhere in the world, locals know the roads so tend to drive faster than visitors. I would prefer NOT to get a speeding ticket in a foreign country, so I disregard the cars behind me and drive only a few km faster than the posted speed limit. Sometimes I pull over to let cars pass me (to the annoyance of my navigator).
Towns and villages, especially those with lots of visitors, tend to have pretty good signage about parking, usually on the edge of the town (for example, San Gimignano). Often, especially for bigger towns or small cities (for example, Bologna) we will check Google maps ahead of time and navigate to likely-looking parking garages. More and more, European parking garages in cities tend to be underground, have good lighting, and things like green or red lights showing whether spots are free or taken. You can check that out beforehand. If you want to make sure that you don't have issues with parking, arrange your driving to arrive at your selected village before or after the height of when visitors will be at that village.
We've had issues with the machines gas stations that don't have people at them taking our U.S. credit cards. To avoid this, we make sure to not need gas on a Sunday, when gas stations tend to be closed, and (obviously) only go to gas stations that have people at them. Uniformly, employees (and other users) at gas stations have been helpful if we can't figure out how to get the pump to work.
Yes, you need to avoid driving inside the ZTLs, but we've found it easy to avoid them, especially if we make sure to park in designated parking lots or garages outside the zones.
Especially in parts of Italy like Tuscany, traveling by rental car can provide you with stunningly beautiful views. Take your time, pull over if the driver wants to enjoy the views, and enjoy!
Feel free to provide the names of the village you're considering; I would bet that I, or other Fodorites, could provide specific parking or driving suggestions.
Driving in Tuscany is easy
From your other thread/questions I recommend choosing Pienza as your base
There are a few hotels just outside the walls that have parking and easy access
PM me if you need recommendations, we have stayed in Pienza a few times
There are dozens of threads here that discuss driving in Italy, how and where to pick up/drop off car, etc
I suggest you spend some time reading those then come back with any questions
If you are looking at southern Tuscany - Pienza, Montalcino, Montepulciano, and San Quirico d'Orcia area - then you can train and rent at Chiusi-Chianciano Terme the train station for Chiusi. From here you are probably an hour or so from Pienza and this can limit how much you're driving if you're concerned about driving in big cities or longer distances. Obviously this limits your choice of rental agencies but gets you out in the country before renting the car versus renting someplace like Florence.
If you're looking at more northern Tuscany maybe rent in Siena? Siena is still a big city by Tuscan standards but you are in the country pretty quickly once you drive away from the town itself.
I drove several times in rural Italy before navigation systems became common and that was a whole other experience. With a navigation system or the ability to connect your phone to the car's screen there will be significantly less mystery in where you are but I would still allow at least 25% drive times to Google maps estimates for driving. And pack a sense of humor and embrace the occasional mystery of what town you entered. The famous towns are famous but that doesn't mean there aren't towns that were just like those before they became famous so explore on your own if something looks interesting.
And my biggest advice is the hardest - slow down and try to experience a bit of the peacefulness of rural life. Everyone wants to see 2 villages a day, take the pictures and are racing around but some of the real charm is how much you can start to feel at ease. It's hard on vacation with limited days but isn't also what vacations are supposed to be about?
Have a great trip, rural Tuscany is as beautiful as advertised,
=Tod
Trains/buses go to all the little towns in Tuscany. People live in these places and many depend on public transportation. It just takes longer to get around than driving yourself, but personally I prefer it.