Agriturismo in Tuscany

Podere Cunina in Buonconvento. We were there in 2022 and loved it so much we are going back in September. They are not a winery, but they do produce olive oil, honey, and saffron. They are located in Buonconvento, just south of Siena. Buonconvento is about 20 mins from Montalcino and maybe 45 mins from Montepulciano. When we were there, we stayed two nights in Montepulciano. We visited Avignonese winery. We had a car but hired a driver. Then we drove to Podere Cunina. They offer a wine tour which we did and visited three wineries in Montalcino in one day - had lunch at the middle one.
That was a great day! Also Siena is just a two-stop train ride away. We left our car at the train station in Buonconvento and did a very easy day-trip to Siena by train. We highly recommend this agriturismo!

https://www.agriturismopoderecunina.com/

We stayed at Fonte Bertusi in Pienza and from there took trips wo Montepulciano, Montalcino, cheese farm, wineries, cooking class etc. Their website is very accurate. Wonderful breakfasts and wonderful hosts.

I recommend Castello di Verrazzano . We spent a wonderful week in Chianti using it as a home base. The food and service was excellent! Be sure to sign up for their wine tour, followed by a food and wine tasting. If possible, do the dinner because you'll be there a while and should not drive afterwards.

From Castello di Verrazzano, which is just outside Greve, we visited Greve, Radda, Castellina in Chianti, Siena, San Gimignano, Volterra and took the local commuter bus for a day trip to Florence. We also visited Abbazia di Monte Oliveto Maggiore. It's a gorgeous monastery. We visited in the afternoon, went to a small restaurant nearby for dinner, then returned to attend vespers at the abbey. Vespers is celebrated in Gregorian chant. When we were there in December it was only us, the monks and one lady from a nearby village. The monks invited us to participate in the service by singing the responses. We followed along the Latin as best we could and it didn't take long to get the responses correctly.

For a charming agriturismo winery in Tuscany, I recommend checking out "Locanda La Casina di Lilliano" in Castellina in Chianti. It's surrounded by vineyards and offers modern amenities while preserving a rustic charm. You can find more detailed options and recommendations in this article: 7 Charming Hotels in the Tuscan Countryside. Enjoy your trip!