Your journey begins in Umbertide, along the upper stretches of the Tiber River. The first castle you'll encounter is the Rocca, with rounded crenulated towers and a square tower, the symbol of the city.
Just outside of town is the gorgeous Castello di Civitella Ranieri. Strategically placed, its history is closely intertwined with that of the capitani di ventura, leaders of groups of mercenaries who played an important role in the Middle Ages. Construction on the castle began in 1078, but it only became famous some four centuries later when one of the members of the family, Ruggero II di Ranieri, known as Cane (Dog), reclaimed the castle after it had been taken away from them by the Michelotti family of Perugia.