Where to Stay in Tuscany - Volterra vs. Montepulciano vs. ??

Not knowing if you've driven in Italy, I'll include this. You will need an IDP available at AAA it's basicly a translation of your home license. Required by law in Italy.

Read this and download their e book. Rules of the road and other important info.

https://www.italybeyondtheobvious.com/dont-mess-with-ztl-zones

Faster to train to Florence and pick up a car there then to drive from Milan.

I don't know where you're flying out of, if Milan,
Head to Volterra. If Rome, Montepulciano.

I agree with other poster that u can pick up a car in Florence or better yet pick it up in Siena.
Parking in the villages can be very difficult if not impossible. Make sure when u book lodging that they guide u on where to park. Montepulciano can easily be done by bus from Siena. The walking would be the same. These are hilltop towns with little if any car accessibility. It is good that u are there off season.
Stay in Siena or an agriturismo is my suggestion. This is what we did on our tr8p romTuscany and Umbria, it turned out very good and we were there in summer months even.

Have, over several trips, never had any problem parking. Just follow the signs for parking outside each village to usually several parking areas. Most are located 10-15 minute walk into town.
Some are metered so purchase ticket and put it in your windshield appropriately.
The exception would be Siena, which is usually further from the center of town.

Edit: decide quickly and make reservations for your lodging. This is a busy time in this area.

Does four days include your first day travelling to Tuscany and the day you are leaving Tuscany?
It's too big an area to see so much of it with only three nights available. Concentrate on the Chianti area or the Val d'Orcia. I like both but much prefer the latter, nicer villages close together and nicer scenery overall. I've stayed in Montepulciano twice, it was practical for what I wanted to see and with my rentals, though any number of places are suitable - Pienza (a fabulous little place), Cetona, San Quirico. I was not as enthralled with Siena as most and would find it too big as a base, especially if using a car, though the area around it is fairly central if you had more time.

One of the rentals I used has since closed, the other one was with this lovely family. A walk uphill into town, downhill after a bit of wine and pasta: https://www.fontecastello.it/

I would suggest staying in Montepulciano. It’s located between the Val d’Orcia and Valdichiana, both UNESCO sites for their beauty. With fantastic scenery, beautiful sunrises and sunsets, amazing restaurants, fantastic wine…Montepulciano has it all.

During this time of year, Montepulciano is lively, but not overrun with tourists. The grape harvest is going on for this year’s Vino Nobile, and the olive harvest should be starting any time now. This is our favorite time to visit Montepulciano!

If you decide Montepulciano is a fit for you, let me know and I can suggest places to stay and restaurants to try.

I hope you and your husband have a great time driving through the Tuscan countryside!

Thank you - this was the type of response I was looking for. My daughter’s in laws have a place in Chianti region but I don’t want to impose. If you could recommend some accommodations, would greatly appreciate it.

I'm not sure if you want to stay in a town but if you're open to an agriturismo a bit outside of town, we stayed at Fonte Bertusi (https://www.fontebertusi.it/) last fall. It's a couple of miles outside of Pienza and about 10 miles from Montepulciano. We loved the property and the hosts - we would definitely return. I can't say what their last minute availability might be but they have several apartments.

Thanks - we are open to staying in the countryside!

We've stayed here several times, have tried other locations, but keep returning. Iit just feels like our home away from home. An 1:15 from Volterra, 45 min from Montepulciano. Very centrally located for central and southern Tuscany.
http://www.borgorapale.it
Fantastic hosts.

I have twice stayed at the beautiful Politian Apartments in Montepulciano, both times with a rental car. The apartments are lovely, spacious, gorgeous views out of the large windows and with gracious owners who have created a wonderful place at the "top" of town. They will give you a placard to place in your car which enables you to park for free in the street right by the apartments. Following their careful directions, it's less than 5 minutes to be out on the road to other towns in Tuscany. https://politian.business.site/

Thanks, I will check out the rentals. I have also found a couple of places on VRBO.

We stayed five nights at https://www.terredinano.com/en/ which is between Montepulciano and Pienza...beautiful views and accommodations, wonderful food. Easy to do day trips to surrounding villages.