San Leo, a magnificent art capital, mentioned by Dante Alighieri in the Divine Comedy, is the heart of the historical region of Montefeltro and the town that gave it its name.

Located in the Province of Rimini, in (now) Emilia Romagna, it is a destination truly “Off the Beaten Path!” Undoubtedly an exciting destination. The mighty limestone boulder of San Leo constitutes in itself a natural fortress. It can be seen from far away on top of a rocky mass with sheer sides. It has led to its dual military and religious importance since prehistoric times, as seen by its prize architectural and artistic artifacts.

Famed for various historical and geopolitical events, it has been the location for documentaries and films, are a popular tourist destination and a jewel of the province of Rimini. Yet, to this day, the rigor and beauty of the old town have remained intact.

It boasts several Romanesque buildings like the parish church, cathedral, and tower, along with several Renaissance buildings like the Medici Palace, which houses the elegant Museum of Sacred Art, the Severini-Nardini Counts residence Palazzo Della Rovere, now the town hall.

The Fortress was bitterly disputed by the Byzantines, Goths, Franks, and Lombards during the Middle Ages.

In 1441, the very young Federico da Montefeltro conquered the Rocca of San Leo.

In the meantime, the art of war had known decisive innovations. The Fortress, with its medieval structure, composed of simple quadrangular towers with slopes arranged in the enclosure of the central keep, was no longer able to support the advent of firearms.

Federico da Montefeltro completely redesigned the fort’s architecture and responded to the fire according to dynamic counter-offensive canons that could guarantee crossed fire directions.

The Fortress was equipped with artillery, and the access routes, out of the way of enemy fire, were protected by military outposts. The Fortress thus constituted the culmination of a warlike system that extended to the whole boulder.

And it was here that Federico da Montefeltro spent many years of his life, and where he called his friend Piero Della Francesca and commissioned his famous portrait.

Who doesn’t know this famous portrait, now at the Uffizi in Florence?

The bust of the couple has as a background a landscape that is precisely the landscape that can be admired from the San Leo Castle.

But, of course, the river was much bigger back then.

His wife Battista is pale, has a broad forehead, and a calm expression. Probably painted after her death.

Federico has a bizarre profile: the nose (the nasal bridge) is flattened and falls back unnaturally. It certainly cannot be a mistake by the painter: Piero della Francesca was one of the most gifted artists of his time and a personal friend of Federico. The hooked and broken nose was a scar obtained during a tournament in which he had also lost his right eye: for this reason, he always had himself portrayed in his left profile. As can be seen below.

It was a social media choice, just like those who use social networks such as Instagram or Facebook. However, posting a photo on your profile is rarely an unweighted decision. You always want to look your best.

Although San Leo seems unconquerable, it has been besieged and conquered over the centuries. In fact, San Leo was the domain of the Counts of Montecopiolo, the Da Montefeltro (from the ancient name of San Leo), the Malatesta, the Medici, disputed with the Della Rovere, until the passage under the Papal State in 1631.

From 1631 the Fortress was adapted as a prison in which the narrow cells, obtained from the original military lodgings, were imprisoned by Risorgimento patriots. The most famous were Felice Orsini and Cagliostro.

Even after the unification of Italy, the Fortress continued to fulfill its function as a prison until 1906.

Today, the Fortress, cleaned off the nineteenth-century superstructures that altered its elegant Renaissance lines, has returned to its architectural splendor, making it one of the most celebrated testimonies of military art, in a setting of history and skill among the most beautiful in Italy.