San Leo, the perched village in Romagna

As soon as you glimpse San Leo, a medieval village perched in Romagna, from the winding road, you realize you are in a place different from all the others.
Its imposing fortress dominates the landscape on a high rocky massif: one side of the castle is placed right overhanging the rock and makes the village seem practically inaccessible. Moving forward, here is the entrance. Entering by car, you travel along a narrow road that climbs up the side of the large rock.
These are my first impressions. I want to convey them to you to make you imagine this very special place, one of the Orange Flag Villages of Emilia Romagna, also listed among the most beautiful Villages in Italy.
I had been thinking about visiting it for a while…

COSA TROVERAI IN QUESTO POST:
The medieval village of San Leo
The medieval village of San Leo is paved with stone and you can breathe a relaxed air that has the scent of ancient times. Here life flows calmly and slowly. It is a fortified town, which stands right on a spur of limestone-arenaceous rock, in the pulsating heart of Montefeltro, a historic border land, cultural scene and cradle of unparalleled gastronomic products.
Historical notes
It is precisely the extraordinary conformation and position of the village that has determined, since prehistoric times, the military and religious value, as is also demonstrated by the findings in the area of artifacts of great value.
The village takes its name from San Leone who, arriving together with San Marino from the coasts of Dalmatia, is said to have converted the inhabitants to Christianity, becoming their first bishop. But the town, as anticipated, has much more ancient origins….

In Roman times the village was called Monte Feltro, from Mons Feretrus. The name is linked to the settlement that arose around the temple consecrated to Jupiter Feretrio.
It was a constant object of contention, until the conquest in 1441 by the young Federico da Montefeltro, who harshly opposed the Malatesta in the dominion of the Marecchia Valley.
The village is also distinguished by the illustrious guests who passed through its alleys and who, like Dante Alighieri and Saint Francis of Assisi, sometimes settled there. In 1631 it was devolved to the Papal State, and became the site of a prison where the Count of Cagliostro first (1795) and then Felice Orsini (1844) ended their days.


San Leo Castle
The Rocca di San Leo, located on a cliff of almost 600 meters, dominates the landscape with an appearance that varies between the bow of a ship and a fairy-tale castle.
Although it can be reached by shuttle, I recommend walking up a wooded path to better appreciate the view of Romagna.
The imposing structure, with two towers and a high surrounding wall, offers an immersive experience: for 9 euros you can visit it with a tablet-guide, exploring parade grounds, tunnels, towers and panoramic walkways

The interior of the Castle
The interior rooms of the Rocca di San Leo, stripped of their 19th-century furnishings, retain their Renaissance charm. You can visit the rooms on multiple levels, the garrison rooms, the treasure cell, the detention cells of figures such as Felice Orsini and Count Cagliostro, and the torture rooms.
The Fortress Museum displays paintings, prints, furniture, ceramics, historical documents on the protagonists of San Leo and a collection of weapons and armor from 1300 to 1800.

The perched medieval village
The village with ancient origins is positioned a little lower on the same rock mass where the Rocca stands. Listed among “The Most Beautiful Villages in Italy,” the marvelous historic center unleashes its charm in every period of the year, starting from its pulsating heart, the square, dedicated to the Supreme Poet (Dante), which gathers around itself the nucleus of the medieval city.

What to see in the medieval village
In addition to the suggestive fortress, you can see the ancient Romanesque buildings such as the Pieve, the adjacent Duomo with Romanesque-Lombard shapes, built with sandstone, which rises close to the cliff’s overhang and the Civic Tower of probable Byzantine origin, with a quadrangular base, which is located inside the Archaeological Park. They are flanked by numerous Renaissance buildings, such as the Palazzo Mediceo which houses the elegant Museum of Sacred Art.
The latter hosted Saint Francis in 1213 who received the gift of Mount La Verna there.
From San Leo, through its alleys that spill out onto the perimeter of the town, you can enjoy the view of the surrounding mountains from various observation points along the Marecchia valley to the sea 30 km away as the crow flies.
Although the village is small, it is very rich in history and architectural beauties that I recommend you discover. Getting lost in its empty streets was a delight, wherever you looked, you encountered glimpses of incredible beauty!
Typical Products of Romagna
It takes its name from one of its famous guests “the Balsamo di Cagliostro” a herbal liqueur typical of this town, and is the first of the long series of typical delicacies that you can find in these areas.
The typical Honey is also an elite product of the area, produced by beekeepers from Leonine.
The Piadina Romagnola is a must, which you can also enjoy while walking around the village, the cherries of Valmarecchia.
For more information on typical products and much more visit the Guida di San Leo website.



For further information, visit the official website of the IAT where you will also find all the updates of the new tourist provisions.
To read other articles on the villages of Romagna, I invite you to consult my dedicated page “Emilia Romagna“, by clicking here.
I also point out that a short distance from here, the Castello di Montebello also deserves a visit, also known as the Castello di Azzurrina because of the ghost that lives there.
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