Castiglione del Lago. Castiglione del Lago has been constructed on a limestone cliff cape on the east side of the Trasimeno Lake. Etrurians were probably the first to occupy this area, as confirmed by the findings of tombs in the area.
After the Roman occupation, the village belonged respectively to the marquis of Tuscany, to the abbey of S.Germano from Campoleone, to Perugia, to the Duke Della Corgna until 1647, again to the grand-duke of Tuscany and, in the XVIII century to the Papal State. Inside the urban center, the middle age town walls, the Town hall and the palace of Della Corgna Dukes are still well preserved. The most fascinating building of all the village is without any doubt the castle which, with its four towers, represents one of the most remarkable examples of military art in Umbria.
Passignano sul Trasimeno. The most ancient nucleus of Passignano sul Trasimeno is still today encircled by the middle age walls which testify the development the center underwent during the Roman Empire, evolving from a small agricultural village to a castle, which, after the Lordship of Uguccione II in the 917, was constantly aimed at by Arezzo, Perugia and Florence.
Tuoro sul Trasimeno. Rises exactly where the battle of the Trasimeno between the army of Rome and that of Cartagine leaded by Hannibal was carried out. The foundation of the village is, however, much more recent, as the first testimonies of the village date back to the XIV the century.
Magione. The name of Magione, which was first mentioned in 1075, derives from the Castle of the Knights of Malta. Today this building rises in the middle of modern urban center, and is characterized by a square plant with circular towers and a courtyard on which, on the three sides, three overlapped loggias appear.

Città della Pieve. This characteristic village was touched by the events of the medieval history, and indeed, a number of masters had the control of the town until when Clement VII placed it under the direct control of the Church. At the center of the village, still today encircled to a good extension by the walls of 1300, having such a medieval style that here the narrowest street of Italy can be found (via Baciadonne), the Dome dedicated to the SS. Gervasio and and Protasio rises. Inside the church, works can be found of Domenico Alfani and of two great painters from Città della Pieve, the Perugino and the Pomarancio. Some works of the most famous painter of the city, Peter Vannucci, are conserved in the churches of S. Maria dei Servi e S. Antonio Abbate.
Perugia. The great "Guelf strong-hold" rises up in the region's heart, with its 5 storical quarters closed-in by its Etruscan town walls. These enormous bastions formed by cyclopic square masses, were constructed 22 centuries ago and are still visible for long stretches. Entering the city via Porta San Pietro, whose exterior was remodelled by Agostino di Duccio in 1475, you'll arrive at the basilica of St. Dominic on the right-hand side; the very important National Archeological Museum of Umbria is to be found in the adjacent cloisters and convent. Continuing along, you'll reach the Piazza del Sopramuro, where the 15th century Palace of the Old University and the adjacent Palace of the People's Captain look down on the square. Further on, after a short climb, you'll find yourself in one of Italy's most important squares, where you'll see the Priors'Palace, the Cathedral and the 13th century fountain Major Fountain at the center. At the extreme end of Corso Vannucci you'll find famous panoramic gardens built on the foundations of the Rocca Paolina, a strong-hold built by Pope Paul III in 1540.

This itinerary lies in a typical Tuscan landscape. It starts from the town of Cortona, that is rich of architectural and artistic heritage and, also, is the native place of the distinguished artist Petro da Cortona; and it ends in Siena, the famous city of art.
It proceeds among the green valleys of Valdichiana and the gently rolling hills around Siena. On your way, you will see some marvellous medieval monuments, like the abbey of the mount Oliveto Maggiore, the church of S.Antimo and the one of Farneta. Also, you will visit the towns of Pienza and Montepulciano. Practically, at every stage of your way there will be something interesting and curious to admire: for example, the unique landscape of Asciano, or the beautiful fortress of Montalcino.