Begin the day with a walk-through San Quirico D’Orcia, a village made famous by the coronation of Holy Roman Emperor Frederick II. It continues to draw travelers due to its location on the Via Francigina, which is the pilgrimage road to Rome. After we go to the countryside of Pienza to visit a local cheese farm specializing in the region’s prized Pecorino di Pienza. Meet the cheesemakers and enjoy a guided lunch tasting paired with local wines and seasonal delights. We will conclude the afternoon with free time in Pienza, the “ideal city” of the Renaissance. Enjoy free time to explore the local artisan shops. Meander its charming stone alleys, admire sweeping views over the valley, and learn about Pope Pius II’s vision for a utopian town. We will then head back to the castle before resting for our local dinner out.

Discover the agricultural traditions that have shaped life in the Tuscan countryside for centuries with this immersive experience in the village of Serre di Rapolano. The day begins at Pereto, a local organic agricultural estate surrounded by rolling hills and olive groves. Guests will enjoy a private visit of the farm to learn about the cultivation of ancient grains, legumes, and wheat, along with the production of artisanal flour products and beer using sustainable zero-kilometer practices. A light seasonal lunch featuring products from the estate will be served on the property. Following the visit, we continue through Pereto’s olive groves to explore the importance of olive cultivation and olive oil production in Tuscan culture. In the afternoon, we return to the historic center of Serre di Rapolano to visit the Museo dell’Antica Grancia e dell’Olio, housed inside a medieval fortified granary that once belonged to Siena’s Santa Maria della Scala hospital system. Here, guests will discover the ancient olive press with its original machinery and millstones, along with the historic grain storage areas that once supplied Siena through an important agricultural network. This experience offers a unique opportunity to connect Tuscany’s past and present through food, farming traditions, and local history in one of the region’s most authentic and lesser-known villages. We will go home to rest before dinner out locally.

Roll up your sleeves for a hands-on Tuscan cooking class in a rustic farmhouse kitchen. Under the guidance of a local chef, you’ll harvest herbs and vegetables from the garden, knead fresh pasta, and master classic recipes passed down through generations. After the preparation, sit down with your fellow cooks to enjoy the fruits of your labor over a leisurely lunch—with plenty of local wine and laughter to go around. We will return home with full bellies to rest and relax bfore a light dinner out in the village.

Today you can start with a leisurely morning at the castle, where you can bask in the tranquility of your surroundings. Whether you choose to relax on site or venture out on foot to nearby destinations, the morning is yours to savor. A formal lunch today is not planned so if you would like to grab a lunch in town, you can. We will start our early afternoon outing heading to the picturesque town of Cortona. Experience the essence of Italian life with a "passeggiata," a leisurely stroll through charming streets lined with historic buildings and boutique shops. Absorb the beauty of this hilltop town and immerse yourself in the local atmosphere. Later, we transition to a truly special evening as we head to a winery for our farewell dinner and wine tasting of beautifully made Syrah wines and dishes that harmoniously blends local flavors with the deep tradition of hospitality.