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.
Some 6 km further on you'll find the Rocca d'Aries. Built by the Fortebracci family to replace an older fortress, it first served a military purpose but then became a residence, and it too is closely tied to the events surrounding the era's most famous capitano. From here you should head to Pietralunga, another small town built up around a fortress and entirely embraced by defensive walls that date to the 8th century. End your journey here with a lovely dinner of classic truffled gnocchi made with traditional Pietralunga potatoes. Or you can set of on another journey right away, just like a real capitano di ventura.