Once in Monte San Savino from Civitella (or via the railway line Arezzo-Sinalunga), the journey continues towards the Castle of Calcione for a short but quite demanding stretch.

Take the SS73 towards the Dreini area. Here, at the mid-point along the stretch, is the Osteria del Cacciatore restaurant. From this reference point continuing uphill along the main road, you can make a detour to the Castle of Gargonza, reachable by a dirt road on the right 800 meters from the restaurant. The fortified village of the Castle of Gargonza has medieval origin, belonging to the Corsi Salviati family since 1696, who transformed it into an organized farm with land managed by sharecropping. Due to its strategic position, it was often disputed between Florence and the Republic of Siena. Furthermore, according to some historians, Dante Alighieri spent the first days of his exile here in 1303. In the first half of the 19th Century the village housed over 500 people, but was later abandoned and restored around 1970 by the current owners, becoming one of the first accommodation facilities in Tuscany born from the architectural recovery of important historical monuments.

To reach the Castle of Calcione we must instead continue on the SP24. We gently begin to descend the hill, entering the municipality of Lucignano, along a road lined with flourishing oaks, which only in the proximity of the Castle leave room for a few fleeting views of the panorama below. After about 5 km on the left is the tree-lined entrance to the ancient fortified village. Built in the 10th century, the Castello del Calcione is a private estate comprising a main building, five farmhouses, a church and three small lakes on an area of ​​2,400 hectares. From an architectural point of view, the structure of the castle has not changed since the beginning of the 15th Century, although unfortunately two of its four towers were destroyed in the first half of that century.