San Leo, the hamlet on a rock

San Leo, the hamlet on a rock

by /// August 31, 2021 /// Estimated reading time: 5 minutes







A village, a fortress perched on a limestone and sandstone spur in the heart of the Montefeltro area.
A border land, a theatre of cultural and ecclesiastical history. This, in a nutshell, is San Leo.

Its timeless charm has earned it the right to join the Borghi più Belli d’Italia (the association of Italy’s most beautiful little towns) as well as Orange Flag status. You can find it on the map in the upper Valmarecchia, inland from Rimini, nestling between Tuscany, the Marche and San Marino.

A visit to San Leo is a journey through history and culture – from the time of St Leo to the visit of St Francis, from the incarceration of Cagliostro and Orsini to the inspiration of Dante and the landscapes of Piero della Francesca.

San Leo is a place of outstanding cultural richness and natural beauty. It is a veritable vision all year round, especially at sunrise or sunset. Its remarkable form, with its walls teetering 600 metres up on the clifftops, has always endowed it with a dual military and religious importance.

San Leo is still an almost impregnable place, in a perpetual balancing act between the surrounding topography and the human hands that have shaped its characteristic fortress silhouette. Among the hills dotted with small settlements, a single road chiselled into the rock winds its way up to the village.

Inside the old gate, the pale, sand-coloured stone buildings exude a tranquil, other-worldly mood with alleys and corners laced with poetry.
The castle looming over the cliff edge, in a panorama of woodlands and rocky peaks marching out to the Adriatic, resembles a boat tossed on a rocky sea and a fairy castle rising from the mists. Being a few degrees cooler than its surroundings, on account of its lofty position, it is a perfect destination for anyone seeking a fresh, relaxing contrast to the Romagna Riviera.

San Leo, view of the fortress Ph. carlo_grifone

San Leo, view of the fortress Ph. carlo_grifone


The village is named after St Leo, its patron saint.
The slab of rock holding it up lends its name to the whole area – the Montefeltro, from the Latin Mons Feretri, a Roman settlement built around a temple to Jupiter Feretrius (tradition has it that the temple is under the contemporary cathedral.)

In the Middle Ages, it was fought over by the Byzantines, Goths, Franks and Longobards, becoming the capital of Berengar II’s kingdom in the mid 10th century.

The Malatesta of Rimini and their fierce foes, the Montefeltro of Urbino, snatched it from one another in the 13th and 14th centuries; the Montefeltro finally prevailed in 1441 through Duke Federico.

San Leo was part of the Marche region until 15 August 2009, when it joined Rimini province along with six other municipalities in the High Valmarecchia area after a referendum.

What to see

San Leo’s most striking feature is undoubtedly its impressive castle towering at an altitude of 639 m over the imposing rock walls that have made it impregnable.
The museum has a fascinating collection of prints, paintings, furniture and ceramics along with extensive records on the key figures in the village’s history, from Berengar to Montefeltro. You can also visit an exhibition of weapons and armour from the 14th to the 19th centuries, along with the dungeon, including Cagliostro’s cell.

San Leo, Fortress Ph. carlo_grifone

San Leo, Fortress Ph. carlo_grifone

The village’s oldest building is the parish church. Built in the Carolingian era and remodelled in Romanesque stone, it stands on the original cell where St Leo retired in prayer and lived his last few years as a hermit. It is made of material retrieved from the Roman era, in a basilica plan with three aisles demarked by pillars and columns.

The nearby cathedral, dedicated to St Leo, was erected near the cliff edge in the 7th century and completely renovated in 1173 in sandstone in a Lombard Romanesque style. The mighty square bell tower, probably of Byzantine origin, offers some superb views over the village.

The Medici Palace, built on behalf of the Republic of Florence for the governor of San Leo and Montefeltro, now houses the Museum of Sacred Art and the picture gallery. The museum offers artworks and furnishings from various churches from the 9th to the 18th century, while the gallery contains works by Guercino and Caravaggio, among others.

Piazza Dante – the central square dedicated to Italy’s greatest poet – is the heart of the medieval village. The town hall, Palazzo Della Rovere, has an elegant façade; this is where the Sanctuary of La Verna was donated to St Francis as a gift in 1213.

About a mile or so from the hamlet stands the monastery of St Igne, considered to have been founded by St Francis. It dates back to the 13th century, and its cloister contains a piece of the trunk of the oak under which the saint preached.

San Leo, view of the village Ph. carlo_grifone

San Leo, view of the village Ph. carlo_grifone

What to do

Spring – Explore the San Leo area from the sky with a paraglider or hang-glider from the Mount San Severino crag.
Summer – Go hunting for the landscapes that inspired artist Piero della Francesca, perhaps on a guided tour of Montefeltro’s Renaissance scenes with the Balconi di Piero viewpoints.
Autumn – Discover Montefeltro’s natural heritage with a visit to the nearby Sasso Simone and Simoncello Natural Park.
Winter – Explore the village, which is often wreathed in an atmospheric mist, and visit the the Christmas market during the festive season in nearby Sant’Agata Feltria.


Cherry Festival – last weekend of May
The Festa dal Zarisi is a traditional festival of a delicious local product, just down the valley in Pietracuta di San Leo.

San Leo festival – July-August
This prestigious musical and cultural event has always embraced a variety of genres. Performances are staged in the Romanesque cathedral and in the great castle tower.

AlchimiAlchimie – late August
Several days devoted to celebrating Giuseppe Balsamo, the Count of Cagliostro, as magic and esotericism fill the old streets with themed markets, music, fireworks and dance.

Food and Wine

The Montefeltro area offers not only cultural treasures but also fine food and wine.
For a traditional menu of local delicacies, try San Leo tortelloni followed by rabbit with wild fennel, Cagliostro-style casserole, and pecorino cheese wrapped in walnut leaves with a few drops of Valmarecchia honey, all washed down with a Sangiovese Superiore PDO Colli di Rimini.
Round off the meal in style with a glass of Balsamo di Cagliostro, the village’s traditional digestif made from liquorice root, invented, as legend would have it, by the count himself.

Famous characters

Cagliostro – The Count, who is also mentioned in the Divine Comedy and whose fame as a healer and alchemist reached the most important courts in Europe, was imprisoned in the castle dungeon for heresy and sedition.
Felice Orsini – The revolutionary and follower of Mazzini born in nearby Meldola is known for his attempt to assassinate Emperor Napoleon III in Paris. Four years earlier, he had been incarcerated with his father and other Roman patriots in the “Fort of Saint Leo, where incorrigible revolutionary convicts are imprisoned”. St Leo, the village’s patron saint, came here in the late 3rd century ad from Dalmatia to escape Emperor Diocletian’s persecution of the Christians.
St Francis – On 8 May 1213, Count Orlando Catani of Chiusi in Casentino gave St Francis the gift of Mount Verna, where the Sanctuary of the Verna was built; this is where he received the stigmata. The saint’s image has been incorporated in the town’s coat of arms, and the villagers commemorate the donation in a celebration every May.

Pilgrim paths and walking trails

Keen trekkers on the lookout for new excursions may be interested to know that San Leo is the departure point for the 3rd stage of the St Francis Way, from Rimini to La Verna.

The [Emilia Romagna Villages] section is dedicated to Villages that are part of the Associations Borghi più belli d’Italia, Bandiere Arancioni del Touring Club & Borghi autentici d’Italia.


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