Tuscany

You can drop the car either in Chiusi or in Orvieto, but check the opening times.

Florence is in Tuscany, it's the regional capital of the Region. Maybe you mean the postcard countryside south of Florence that's around Siena and along the SS222 road.

Thank you! Yes, I guess I mean the much broader area of the many smaller towns south of Florence - novice here! Siena seems highly recommended, as does San Gimignano and Montepulciano. Not sure what a logical flow would be, and if it makes sense to take day trips from a home base or move around. TIA!

The driving distances aren’t too bad that you need to move around every night. We averaged about 90 minutes of driving a day while staying outside of Montepulciano, but we didn’t go to Siena which would’ve been further. Depending on what towns you want to see I would suggest picking one home base (maybe 2 if you have 2 different clusters of sights to see or don’t mind repacking again).

Siena has rental cars as well so you could take the train from Florence and then rent your car on departure from Siena. Or rent in Florence and see San Gimignano on the way south.

If you rent from Avis/Budget then Chiusi could be a logical drop off location with direct trains to Rome. It is a very small office and closes midday for several hours but is right down the street from the train station. From my research Arezzo and Grosetto (I think) also have Avis locations that could be useful depending on your route.

We spent 8 days in Tuscany, staying at an agriturismo just outside the village of Greve. We had a wonderful time. We visited, Radda, Siena, San Gimignano, Volterra, Castellina, Asciano and the Abbey of Monte Oliveto Maggiore. We also took the bus for a day trip in Florence. We loved staying in one place, not having to pack and unpack.

I suggest you look for an agriturismo near Siena. Take a bus or train to Siena from Florence, then rent the car there. Then, return the car and take the train from Siena to Rome.

We are in Italy now and decided on this trip not to rent a vehicle, but to stay in Florence and take day trips into Tuscany.

The last time we went in 2018, we traveled from the Cinque Terre to Florence by train, stayed two nights, and then rented from the Florence airport and drove through Chianti and stayed at a B&B 20km north of Siena, returning the rental in Siena and hopped a train to Rome. If I had to do it over again, I would have turned the rental in at Chiusi and took the train directly to Rome.

Driving in Tuscany is necessary if you want to see the smaller towns, but not necessary if you are going between larger cities (say Florence and Siena). This trip, we didn’t want to drive, so we took day trips and hired a private guide to take us through the Val D’Orcia region. This was especially good for us as we wanted to wine taste.