From the village of Pietraia, the route moves towards Cortona along a short stretch, but with a remarkable uphill gradient. Along the way, you will pass through several places or points worthy of mention:

• Ossaia, a place known for the passage of the troops of the Carthaginian General Hannibal, which collided with the Roman army of the Consul Flaminio in the ferocious Battle of Trasimeno in 217 BC. From here it is worth taking a detour a few hundred meters from the path and climbing the hill of Sepoltaglia, where there are the ruins of the Church of San Donato surrounded by olive trees, a building dating back to around the year 1000, from which you can enjoy a splendid view of the valley and, if you feel inspired, imagine the battle between the Carthaginians and the Romans;
• Pieve di San Michele Arcangelo, an ancient suggestive and isolated Romanesque church of the 11th Century with three naves and semicircular apses;
• Palazzone di Cortona, an ancient monumental villa from the 1500s surmounted by a large tower and surrounded by walls, also preserving a large Italian-style hanging garden in its premises. Donated by Count Passerini to the Scuola Normale Superiore of Pisa, today it is a center for educational activities and conferences of national and international importance.

From Palazzone the road keeps climbing up the hill towards Cortona, giving us a magnificent view over the Valdichiana. You enter Cortona along Via Nazionale which leads directly to Piazza della Repubblica where the symbol of the city, Palazzo Comunale (the town hall), stands with its clock tower. There are numerous attractions in Cortona that deserve a visit: the MAEC (Museum of the Etruscan Academy), which preserves the tabula Cortonensis,  the Fortress of Girifalco built for military purposes, and the Sanctuary of Santa Margherita, patron saint of the city. Not too far from themain route, about 4 km away, stands the suggestive Franciscan Hermitage "Le Celle", a convent built by St. Francis of Assisi in 1211.

In the lower part of Cortona, in the Camucia station, you can take advantage of the bike-train interchange along the Rome-Florence railway line to move across the territory of Valdichiana.