San Casciano in Val di Pesa to Rome -- Scenic Drive through Tuscany

It is possible to do San Casciano > San Gimignano > Siena > Montepulciano > Rome, but it is a lot to visit in a day only, So you might need to curb your enthusiasm and remove some of the stops.

SR222 is not along the itinerary, it would be a detour which will increase the travel time.

If you plot your itinerary in the order above, you will see what the most efficient route is.

Freeway concessions in the Service Area stops (Autogrill or any other of the chains which have the concession, like Chef Express, Sarni, etc.) never close. You can enter AREA DI SERVIZIO on the Google maps and see where they are located. If you want Autogrill, then put Autogrill in the search box. Most of them will be on the A1 between Chiusi and Rome. Some might be (one at least that I remember) on the freeway from Siena to Sinalunga on the way to Montepulciano, I don’t think it’s Autogrill but I don’t recall.
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Siena is a large city for Tuscany and deserves a full day and I'm not sure what you'll get out of a couple of hours, maybe, parking outside the city and walking in for a quick visit. I would do two places max and it will be faster and easier if these are two smaller places. If you really want see multiple places think about the cluster of small towns like Pienza, Montalcino and Montepulciano together and on the way.

San Gimignano is small and pretty, but very touristy, but fits into your driving path. You could leave early, see SG, drive the 2 hours or so to the Pienza/Montalcino/Montepulciano area and have lunch. And then start on the additional 3 hours or so to Rome. That seems like a full day of driving and sight seeing to me. Keep in mind you probably have at least 5-6 hours of just driving if you stick to the scenic roads between San Casciano and Rome and your town visiting time is in addition to the driving time.

And last but not least you say your hotel is in the center of Rome. Have you driven in big city Italy or the equivalent before? Since a car is often a burden in large cities people often choose to drop off cars outside town and use mass transit or taxis for the last bit to the hotel. If you do drive does your hotel have parking?

My $.02, have a great trip,
=Tod

Hi again, and thank you for the great advice!

You're absolutely right—I don’t think we’ll be able to explore San Gimignano, Siena, and Montepulciano all in one day. We're more interested in enjoying a scenic countryside drive through the vineyards and stopping by one or two charming towns along the way.

I came across this article outlining some beautiful routes in Tuscany:
https://www.tuscanychic.com/tuscany-road-trip/
Do you have any thoughts on the route it suggests? Would it be a good option for a scenic drive from San Casciano to Rome, or do you recommend another route?
Also, could you suggest any specific towns or stops to plug into Google Maps to make the most of the drive?

As for the Rome part:
Thanks for mentioning the challenges of driving in big Italian cities. My hotel in Rome does have parking, but your comment got me thinking about ZTL zones. I’m now considering dropping the car off at Roma Termini and taking a taxi to the hotel instead, to avoid the stress and potential fines. I’ll just need to make sure we arrive at Roma Termini by 5 PM to return the car on time.

Thanks again for your help—really appreciate all the insight!

If you must return the car by 5pm at Termini you don’t have time for much. There is traffic around that time in Rome and on the GRA and on the tangenziale Tiburtina, so even if you stop nowhere and take the freeway, you will need at least 4+ hours, assuming bio stops along the way and refueling before returning the car. Those time are valid if you know where you are going in Rome, if you don’t,, then plan for more.