Travel through the hilly expanses of the old vineyards and olive groves, which characterize the splendid Chianti territory until you reach Castellina. This characteristic ancient hamlet is perched on a hill, where you will visit a historical cellar. Just outside the village, you will be guided through a tasting of different wines of the Chianti area, extra virgin olive oil on Tuscan bread, vin santo with 'cantuccini' and locally produced lavender honey. Then proceed along a panoramic road to the village of Monteriggioni, a small medieval jewel still surrounded by its ancient walls. Further, see the unmistakable clay landscape of the Crete Senesi.

Continuing, reach Val d'Orcia, a UNESCO World Heritage location along the famous 'Via Francigena' route with picturesque landscapes of hills dotted with cypresses, castles and churches. Here, in a historic farm, you will enjoy a guided lunch-tasting of the renowned Rosso di Montalcino, Brunello and Supertuscan wines with a selection of typical products of the territory and a delicious homemade fruit pie.

After a stop in the medieval village of Montalcino, journey to Montepulciano, renowned for its Noble wine obtained from the surrounding vineyards.