Cliffside City


San Leo: Cliffside City

Mary Elizabeth Collins


Soak up some history in this beautifully preserved medieval Italian town, where you can wander around, admiring the old buildings and cobblestone streets, stopping at a terrazza to enjoy a good café ristretto or a glass of vino bianco di Castelfranco Emilia.


Italy never ceases to amaze visitors. It thrills and astonishes, and just when you think you can no longer be moved by any environment, you find a new place in Italy to fall in love with. San Leo is such a place. Set in the province of Rimini, south of the Emilia-Romagna region, it is a small medieval town, perfectly preserved, and its loveliness and location blow travelers away. Author Umberto Eco pronounced it Italy’s most beautiful city, and once you experience San Leo, you can’t help but agree.
San Leo

Access to the city is through a road carved in rock, and the city itself is on Mount Montefeltro, set upon an impressive cliff, more than 590 feet from the ground. San Leo owes its name to Saint Leo the Great, who negotiated with Attila the Hun in 452, to avoid the sacking and destruction of Rome. On the upper side of the mountain, rises the old castle designed by the famous architect Francesco di Giorgio Martini, during the Renaissance, by request of Federico da Montefeltro, the Duke of Urbino. Federico was possibly one of the most renowned condottieri in Italy. He was portrayed with his wife, Battista Sforza, by painter Piero della Francesca, in a famous diptych displayed at the Uffizi Gallery in Florence.

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Because of its beauty and historical importance, Forte di San Leo is the town’s most visited building. From the 18th to the 20th century, it held a prison—in which Giuseppe Balsamo, the Count of Cagliostro and an alchemist and scholar of esoteric sciences, was incarcerated and afterward executed by the Inquisition. Saint Francis of Assisi spent some time in San Leo, founding Sant’Igne monastery there, in the 13th century. A fragment from the trunk of the elm tree where the saint preached is still kept there. Dante Alighieri and Niccolò Machiavelli spent time in the city as well.
San Leo

Aside from the castle, another building not to miss is the cathedral, with its clear Romanesque influences, and the bell tower built directly on the rock, with a view of Mount Guardia, one of the peaks that dominate San Leo. Built in the 9th century, the old church is another must-see building, the oldest monument in the whole territory of Montefeltro, a sublime expression of Romanesque architecture. The Renaissance Palazzo Medici, built between 1517 and 1523, is another marvel to visit. Though perhaps it’s best just to wander around, admiring the old structures and cobblestone-paved streets, entering medieval passages and stopping at a terrazza to enjoy a good café ristretto or a glass of vino bianco di Castelfranco Emilia.

Though there are plenty of hotel options in the area, including a few luxury lodgings, I personally recommend the Grand Hotel Rimini, less than 16 miles from San Leo. It’s a luxurious five-star hotel with a long history. For dinner, nothing beats Il Chiosco di Bacco, in nearby Torriana. Daniela and Roberto offer praiseworthy traditional Italian cuisine, in a uniquely elegant dining hall that is open to the garden in summer months.  ■


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