The Views From This Italian City Will Take Your Breath Away

Picture yourself walking through the streets of a town that looks like a medieval film set. Where— just like in a movie—you can hear the story of a count locked away in the fortress, where he died after years in prison. Except that nothing here is fake, and each stone in this town tells us about centuries and centuries of Italian history. San Leo, which is part of the “Most Beautiful Towns in Italy” circuit, is perched in a panoramic position that will take your breath away. It was built on a limestone massif and the only way to access it is a road carved in the rock.

We are in the province of Rimini, in the region of Emilia-Romagna, known for its fashionable beaches, but here you can admire the sea only from a distance. It is a strip at the end of the Marecchia valley, surrounded by mountains and a territory dotted with the ruins of old castles. San Leo was once the capital of the County of Montefeltro and was the theater of infinite battles. Dante came through here—in the Divine Comedy, and specifically the “Purgatorio,” he mentioned it by name, talking about the difficult climb to the mountain—but St. Francis of Assisi also passed through here.

The most famous name tied to the town, and particularly its unassailable fortress, is that of Count Alessandro di Cagliostro, born Giuseppe Balsamo. An alchemist, occultist, healer and adventurer, this eclectic 18th- century figure was condemned by the Church for heresy and imprisoned for four years (until his death in 1795) in the fortress dominating the Tuscan-Romagna Apennines. And Cagliostro’s prison is the town’s main attraction. Let’s start our tour from here.

- The current appearance of the Fortress of San Leo goes back to the 15th century, when Federico da Montefeltro had the previous stronghold modified to adapt it to new military techniques. Currently a picture gallery and weaponry museum can be visited in the fortress.

- The Pieve di Santa Maria Assunta is the area’s oldest place of worship: construction commenced in the 11th century and what is striking about it is its simple but sturdy stone structure.

- The Romanesque cathedral was built in the 12th century on a hill where artifacts from religious structures going back to the prehistoric era have been found. Inside there is an intimate atmosphere, amid the bare stones, columns and simple bas-reliefs. But its main characteristic is outside. Since the slope on which it was built is so steep, the cathedral has a very asymmetrical appearance and the entrance is not on the façade but on one side: an example of architectural understatement.

Now that the cultural tour is over and you’ve admired the landscape, it’s time to satisfy that growling stomach, and Emilia- Romagna is one of the best regions to do it. Would you rather enjoy a snack as you sit on a bench with a view of the valley? Piadina is exactly what you need. It is a flatbread made of wheat, oil and lard, and it can be stuffed with anything. But the best combination is prosciutto and a typical creamy cheese called Squacquerone. This area is its realm, so there is no bar or stand that can’t make you a truly memorable one.

If you want to sit down at a table and enjoy a proper meal, however, head straight to Osteria La Corte di Berengario II (Via Michele Rosa 74, tel. +39 0541 916145). Go right to the first courses—pasta, naturally—and try something like “Passatelli al formaggio di fossa” or the delicious “Ravioli di Cagliostro” with a sauce of artichokes and black olives. Luckily, you faced the climb to get here, so after lunch the road out of San Leo is all downhill.