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.

Surrounded by these tales of conquest, now head further north, and when you see the little Montecastelli you'll know you're on the right track! Go right to get to Montone, with its lovely fortified medieval structure still intact. The history of this town is closely linked to that of the Fortebracci family, whose most famous son was Braccio da Montone, a capitano di ventura or commander of mercenaries who, in the early 14th century, audaciously struggled to create a domain in central Italy that was independent from the Papal States. When he wasn't fighting, Braccio was something of a patron of the arts and made this little town a cultural hub complete with courtiers.

Montone remains a place of culture and every year hosts the Umbria Film Festival, an important summer event featuring Italian and European film that highlights young talent and encourages research.

A circa 6 chilometri da qui si erge la Rocca d'Aries: eretta dalla famiglia dei Fortebracci su un antico fortilizio, prima con funzione difensiva, poi residenziale, seguì anch'essa le vicende del suo capitano più noto. Da qui, riprendi il sul tuo percorso fino a Pietralunga, piccolo abitato anch'esso strutturato tutto intorno alla rocca centrale e circondato da mura risalenti all'VIII secolo. Puoi concludere il tuo viaggio qui, cenando con un piatto dei classici gnocchi al tartufo, fatti con la tradizionale patata di Pietralunga. O ricominciare subito un altro viaggio, come un vero capitano di ventura.