Agriturismos are Italy's best kept secret. They are independently owned farms that offer amazing food and accommodations. You are basically eating at Nonna's house in the countryside with the food (usually organic) coming straight from the farm. There is usually a coursed menu with fresh just pressed olive oil, wine, and Michelin star level service and food presentation. This is the best way to get to know the people, culture, and cuisine of Tuscany.
You can find agriturismos everywhere but the choices can be overwhelming. As have a couple of recommendations that we highly recommend, all within a 30 min drive of Cipresso e Pietra.
Agrisalotto
This place is an oasis at the foothills of Cortona and Castiglion di Fiorentino. The outdoor seating area allows you views of Cortona and many of the famous hilltops towns. Horses, chickens, goats, and vines surround the property in its serene setting. The appetizer platter does not disappoint and they have one of the best steaks I have eaten in Tuscany. Tender and served rare to perfection. Let us know if you want help booking reservations.
https://www.agrisalotto.it/ristorante/
Podere il Casale
Il Casale is located between Pienza and Montepulciano. It is a woman-owned organic agriturismo that not only offers a restaurant but they also sell their products in a shop on site, will take you on a tour of the farm, and they also offer activities like cheese making, truffle hunting (fall), and a number of other cooking classes.
https://podereilcasale.com/en/the-restaurant/
Tenuta di Paganico
Paganico is located closer to the coast and a little further away (~1 hr from the B&B) but it gives you a chance to see the town of Grossteo and if you are feeling adventurous, the coast of Tuscany further west. It's an organic farm known for their prosciutto and cured meats from the Cinta Sinese pig. The farm tour is a must do because they tell you about their sustainable farming practices including how they breed the farm animals, let them live a full life and their humane end of life rituals and techniques. You can also buy some of the products you will eat at lunch/dinner at their store. Arrive at this place with an empty stomach because you will walk out full, happy, and ready for a nap!
https://www.tenutadipaganico.it/it/