San Leo, the disputed village in the province of Rimini

Perched on an imposing cliff of Montefeltro, the village of San Leo is among the most beautiful in Italy. It owes its name to Saint Leo, who in the 4th century, arriving from Dalmatia with Saint Marinus, evangelized the area and became its first bishop. Tradition has it that the cathedral was built on the site of an ancient temple dedicated to Jupiter Feretrius.

Over the centuries, San Leo was contested by Lombards, Byzantines, the Malatesta, and the Montefeltro, becoming a symbol of power and resistance. Its fortress, later used as a prison by the Papal States, dominates the surrounding valleys, offering spectacular views. With its medieval streets and Romanesque parish churches, San Leo is a village where history, art, and legend intertwine, giving visitors a unique experience between myth and reality.

What to see in San Leo

From its height of almost 600 meters, the fortress of San Leo dominates the Marecchia valley, offering a breathtaking view of woods, gorges, and rocky peaks stretching all the way to the sea. At its feet, the compact village unfolds with cobbled stone streets and a calm atmosphere, surrounded by hills dotted with small towns and lights that glow at sunset.

The historic core is centered around the parish church, built between the 8th and 10th centuries on the site where Saint Leo withdrew for prayer, with naves separated by Roman-era columns. Next to it stands the Romanesque-Lombard cathedral, with a bell tower of probable Byzantine origin, housing a 14th-century Crucifix and columns with Byzantine capitals. The central square is surrounded by historic palaces, including the Della Rovere, the Nardini, and the Mediceo, along with medieval and Renaissance churches and houses.

Imposing, the fortress on the rocky spur tells of centuries of sieges and battles; redesigned in 1479 by Francesco di Giorgio Martini, it was later transformed into a prison of the Papal States. Nearby lies the convent of Sant’Igne, founded in the 13th century and linked to Saint Francis.

Events in the village

San Leo, a medieval village between history and legend, celebrates its traditions with unique events throughout the year. On the last weekend of May, the Cherry Festival returns, a triumph of colors and local flavors. In July, the Harvest Festival takes place, dedicated to the gestures and sounds of rural life. At the end of June, San Leo meets Saint Francis and comes alive with shows and historical reenactments, while the “Giullari del Mondo” bring magic and entertainment to the village streets. AlchimiaAlchimie, at the end of August, celebrates the mystery of Cagliostro and the art of magic, transforming San Leo into a place suspended between history and enchantment.

Discover the places near the village

The surroundings of San Leo offer evocative landscapes and villages rich in history. Not far away is the convent of Sant’Igne, founded in the 13th century, linked to Saint Francis, with frescoes and the trunk of the elm tree under which the saint preached. In the surrounding area, the hills of Montefeltro offer walks through woods, gullies, and ancient villages such as Verucchio and Pennabilli, with medieval alleys and breathtaking views. History enthusiasts can visit castles, fortresses, and Romanesque parish churches scattered throughout the area, while those seeking food and wine experiences can discover wineries, olive mills, and small farmhouses where they can taste typical local products. The combination of nature, art, and tradition makes the surroundings of San Leo an ideal destination for day trips or weekends immersed in the culture and landscapes of the Romagna and Marche hinterland.

Cover photo credits: Wirestock Creators