Rome to Tuscany drive suggestions

We took a train from Rome Termini up to Orvieto--70 minutes. The Hertz office is across the parking lot from the train station there. A very interesting stop is Civita di Bagnorregio just south of Orvieto--a very unique hilltown.

From Orvieto to Siena there are great roads--all controlled access and 4 lane highways. I do suggest you find a place to stay in Siena that has parking as it can be difficult to find parking there.

Outside Siena are many great hilltowns. We especially enjoyed San Gimignano, Certaldo and especially Volterra. We stayed in an agriturisimo there as every farm in the region has rooms and apartments as a secondary income source.

Are you flying into Rome? Where are you flying home from? How many nights will you be in IT? Are you familiar with ITs ZTL zone laws?

We drove from Rome to Tuscany. The first part of the drive was on the A1. The A1 is an autostrada, 4 lane interstate type road.

To maximize the limited time you have, I agree with David. Take the train from Rome to Orvieto and rent a car from Hertz there. Orvieto is a charming town. From Orvieto, take the A1 to SP146 to Montepulciano. From there keep on SP146 to SR2 up to your Airbnb near Siena. This will give you time on your way up to make some stops.

Driving in Tuscany is a real treat. Get your IDP and read up on signage and traffic rules. Also read up on ZTLs. We found ZTLs well marked and easily avoided.

Siena is certainly worth a visit, but I also suggest exploring smaller hill towns. San Gimignano and Volterra are within easy reach.

Check with Hertz regarding the rental car return. From Siena you can drive the famous SR222 to Florence. An alternative would be to return the car in Siena and take the bus to Florence.

When is your trip?

@DougMac,
Any particular reason why we should rent the car in Orvieto and not in Rome?

Our trip is from May 22- 31. We arrive in Rome on the 22, spend 22, 23, 24 in Rome. Pick up the car on 25th early morning, drive to Siena stopping at few scenic sites on the way. 25- 26th night near Siena. 27-28th in Florence. 29-30 nights in CT. 31st morning drive to Milan. Return the car there. Our flight back home is on 31st night.
We have picked Airbnb stays with parking, are familiar with ZTL though this is our first trip to Italy.

We like the idea of driving as it gives us the flexibility of stopping where ever we want plus we will be having a bit of luggage(unavoidable). And we are getting good rates renting the car in Rome.

Renting in Orvieto makes sense. It's easy and convenient. But, if you plan to visit some of the other towns that are so often overlooked, I might rent in Rome. Tarquinia is worth a visit and often overlooked as are other nearby places.
The drive to Montepulciano does not need to be on the highway. Drive the smaller roads and explore the countryside. Do the same on the trip to Sienna. There is really no reason to blast down the Autostrada unless you are in a big hurry and on a vacation in Italy, you should not be. Let your map be your guide.

Any particular reason why we should rent the car in Orvieto and not in Rome?

Your added information paints a very different picture of your trip. I suggested Orvieto because I saw it as a faster way to get to the heart of Tuscany given the limited time you have on the travel day.

As mentioned, you can get from Rome to Siena on a more scenic route than the Autostrada, but it will be a significantly longer drive. I was trying to buy you some time to stop and explore a little instead of having to drive straight through.

How many people will be in the group. Just two? Your plans are ambitious. Having a car in Florence and CT will be problematic. We commuted into Florence from our agriturismo and when we got there I realized what a good choice we had made. For that short period of time, I'd look into parking in the big lot outside the city and taking the tram into town.

I don't know why packing light is unavoidable, but even with a car it will get tiring to lug it around considering the number of stops you plan to make. We just got back from a group trip with a college choir and one of the couples brought a lot of luggage. Even with us being dropped off in front of our accommodations, it was a real struggle for them.

Make sure your luggage is locked in the trunk before you arrive in Siena and don’t leave anything in the car that’s visible.

Appreciate all the responses.

We are aware of the luggage theft issue and of car being broken in. Planned in such a way that we will not take the car to any towns but leave it at the Airbnb and take the public transport into the city. Only place we are in a bit of quandry is Milan. We have the afternoon and the early evening there and we really want to see The Last supper. But we dont intend to book a hotel as we are there for a short time. That means leaving the car in a parking garage with luggage. One option is to look for a luggage storage place but we have not found one yet.

It is a long way from Florence to CT, and the car is a hindrance in CT. It is very true that a car is useful to see three or four Tuscan hill towns in a day. But the car is annoying in the other places. I know you do not believe me, because you use a car at home!

You are covering a lot of ground in a short time, so if that is the definition of success, then you have the right scheme.

My first time in Rome was five nights, and I've been back there many times. (That was Rome-Florence-Venice by train.) It is not a riskless decision to (departure day) drive 3-4 hours to Milan, see the Last Supper (get those tickets immediately), and check in three hours before a flight to the USA. What time is the flight?

You may have a lot of other advance reservations to collect, like every museum, the Coliseum, the Vatican, or whatever. You have no time to wait in the cancellation-hope line.

You could not pay me to attempt to drive in or around Milano...not a chance. I have driven all over Italy but in my opinion, except very early or very late, much like Naples, Milan is one to avoid.
One of my travel stories to tell is of a cab ride I once took there. My driver was passing multi-lanes of slowed traffic on a streetcar track with a streetcar oncoming. While driving like a bat out of absolute hell he was loudly cursing the cars he was passing because they would not let him back into our lane even with an obvious head-on collision with the looming streetcar imminent. I learned a few very choice curse words and also learned that I had not been using several of them properly. The driver was swearing and cursing like a man possessed. There is a certain kind of cadence that these words need in order to be properly exercised. Who knew? This is not about finding a parking spot, avoiding a ZTL or carrying an international license. Driving in Milano is about experiencing life inside of a wild action movie chase scene.
Good luck parking a car in CT....

The train station in Milan has luggage storage. I was in Milan for 1 day to see the last supper. Came in by train, stored luggage, walked around all day, left that night on the train. I also wouldnt want to deal with a car, not because of driving but because its an added nuisance.