Tuscany for 2 weeks in September 2025

Will you have a car?
Almost essential for exploring Tuscan countryside

With 2 weeks I would choose 2 bases-one in Val D’Orcia (Pienza, Montepulciano)
One near Siena
That way you drive time each day is shorter

If you’re planning on staying at an Agriturismo in Tuscany—you will definitely need a rental car to get around this rural area. The charming look of Tuscany comes from its lack of development. And, in agricultural communities, there are far fewer public transit options. That means staying in a town with.bus and/or train stations and realizing that only one or maybe two places each day can be reasonably visited due to the skeletal nature of the public transit system.
To illustrate: To get from Greve-in-Chianti to Siena by public transit takes about 2:10. Driving takes 40 minutes.

Yes we will have a car. I like the idea of two bases. Does anybody have a recommendation for Val D’Orcia (Pienza, Montepulciano)?

Try a forum search
I know agriturismos in that area have been recommended here

We spent a wonderful week at Castello di Verrazano, just outside Greve in December 2015. This makes a great home base to explore the region, including Siena and Florence. There's free parking in Greve and we took the commuter bus into Florence to avoid having to drive. There's also a car park just outside Florence with trams to take you into the city.

Castello di Verrazano is a winery and a great place to stay if you like wine. The rooms are in a building just below the castle and winery. They are very nice and clean but not luxurious in a good way. Isabella, the housekeeper lives in another wing of the building and takes good care of you and the rooms.

Breakfast is served at the restaurant in the castle complex and is an incredible spread. Plan you day to take advantage. For most of the week just before Christmas, we were the only guests and Marco pampered us. At our insistence he sat with us and practiced his English while he taught us some rudimentary Italian. We got so close that we exchanged Christmas presents.

They serve lunch and dinner. I recommend setting aside a day to tour the winery followed by a wonderful unhurried Italian lunch where you sample the wonderful Verrazzano wines.

While there, be sure to visit the Benedictine Abbey of Monte Oliveto di Maggiore. It's lovely! We visited in the afternoon, then went nearby for dinner, returning for evening vespers celebrated in Gregorian Chant. It was a very moving experience. You can see a short clip of it in Rick Steves' Holiday special.

I'm jealous! We'd love to return to Chianti. You'll be there at a good time of the year, there will be many harvest festivals.

We stayed at the favored …..

https://cretaiole.it/en/

Excellent in every regard.

thank you for all your helpful suggestions. I'm excited to explore!