Leaving Cortona, the route stops in Castiglion Fiorentino, another important town in the Valdichiana of Etruscan origin. Along this stretch it is possible to visit Etruscan archaeological sites such as the Melone del Sodo, a complex of two mound tombs of considerable size, where there are tombs and a magnificent funerary altar. This area also joins the transversal section of the path of the White Giant, which crosses the Valdichiana in an east-west direction, cuts the Canale Maestro della Chiana (and therefore also the “Sentiero della Bonifica”) and goes up to Pozzo della Chiana, Marciano della Chiana and Lucignano. From here the transversal path joins the longitudinal one in the area between Calcione and Rigomagno.

Continuing from the Melone del Sodo to Castiglion Fiorentino we find the Castle of Montecchio Vesponi, a well-preserved medieval fortress with crenellated walls interspersed with towers. The presence of a square tower of about thirty meters next to it makes it an important reference point for the whole area. About 4 km from here the route reaches Castiglion Fiorentino whose historic district boasts a series of attractions: the Palazzo Comunale (town hall), the Torre del Cassero, the Palazzo Pretorio, the Logge Vasariane and the Teatro Comunale (municipal theater). Castiglion Fiorentino, like Cortona-Camucia, is also a bike-train interchange point being located along the Rome-Florence railway line.