Medium difficulty stage, not long. We leave the Arno valley to enter the alluvial plain of the Chiana, so the route always keeps close to the hills. It is therefore quite bumpy, not excessively tiring, with no traffic: it almost always develops on dirt or gravel roads.
On the outskirts of Arezzo, the stage begins in Santa Maria delle Grazie, an ancient religious settlement that deserves a careful visit. Leaving the gate of the courtyard area, formerly the cloister of the convent, take Via Andrea della Robbia, up to the underpass of the ring road. Then Via Giulio Salvadori (cyclists follow the Sella municipal road to continue on the Monte Lignano municipal road and arrive at the Pieve La Sassaia di Rigutino; a total of 16.3 km). After a few crossroads there is a small bridge and the locality of San Marco Villalba, where there is a small hostel. Climb up in the middle of an olive grove and arrive near the Bosco di Sargiano natural area. Climb the slopes of Monte Lignano, in the middle of a beautiful wood. Then on partially unpaved and partially paved roads up to the Castle of Policiano. Continuing, you pass the crossroads that takes you back to Santa Maria a Pigli. Immersed for a while in a beautiful olive grove, then in the woods, you cross a small ford and arrive at the Castle of Policiano. There is a flat stretch; then you find yourself mainly in the midst of stupendous olive groves, with continuous ups and downs. Further down the SS 71 Statale Umbro Casentinese Romagnola will be the point of reference up to Orvieto. You need to pay close attention to the signs, even if they are quite numerous and clear, because there are a myriad of paths; having entered a highly anthropized area, you pass in the vicinity of welcoming villas and farmhouses. The path, always easy, retraces an ancient road: it is said that Hannibal also traveled before the battle of Lake Trasimeno. It has evident Etruscan and Roman traces, especially in the retaining walls. With this wonderful landscape full of fantastic colors in your eyes, after several detours you reach the road that from Rigutino leads to Pieve di Sassaia, where you meet an extraordinary hospitable who will make you forget the effort, making available his extraordinary hospitality, cuisine and also the overnight stay. After the stop in Sassaia we continue towards Castiglion Fiorentino, another town that deserves all the attention. From Pieve di Sassaia you return to the houses of Sassaia. (cyclists get off at Rigutino on the SS 71 which they then leave at Vitiano to return to the pedestrian route) Through various country roads you reach Ottavo; then you are in Vitiano; (in Via Cozzano the bikes go towards the SS 71, which they will follow up to Via Palazzo del Pero for 1.6 km). Thus we begin to descend towards Castiglion Fiorentino, cross another stream and arrive on the provincial road. Following it, you arrive at Porta Fiorentina, the entrance to Castiglion Fiorentino.