The menacing fortress of SAN LEO, clamped to the summit of a dizzying precipice in the northern tip of Le Marche, has staggered generations of visitors with its intimidating beauty. Machiavelli praised it, Dante modelled the terrain of his Purgatory on it, and Pietro Bembo considered it Italy’s “most beautiful implement of war”. In fact it’s not as impregnable as it seems; one of the few invaders to have actually been repelled was Cesare Borgia, despite his having first persuaded a weak-willed retainer to give him the key.

Brief history

There’s been a fortress at San Leo since the Romans founded a city on the rock. Later colonizers added to it until the fifteenth century, when Federico da Montefeltro realized that it was no match for the new gunpowder-charged weapons, and set his military architect, Francesco di Giorgio Martini, the task of creating a new one. The walls were built on a slight inward slope and backed with earth, thus reducing the impact of cannonballs. Three large squares were incorporated for the manoeuvring of heavy cannons, and every point was defended with firing posts.

From the eighteenth century San Leo was used as a prison for enemies of the Vatican, of whom the most notorious was the womanizing Count of Cagliostro, a self-proclaimed alchemist, miracle doctor and necromancer. At first the charismatic heretic was incarcerated in a regular prison, but on the insistence of his guards, who were terrified of his diabolic powers, he was moved to the so-called Pozzetto di Cagliostro (Cagliostro’s Well), now the fortress’s most memorable sight. The only entrance was through a trap door in the ceiling, so that food could be lowered to him without the warden running the risk of engaging Cagliostro’s evil eye. There was one window, triple-barred and placed so that the prisoner couldn’t avoid seeing San Leo’s twin churches. Not that this had any effect – Cagliostro died of an apoplectic attack, unrepentant after four years of being virtually buried alive.

The village

As well as the fortress, there’s the pleasant old village to explore. St Leo arrived in the third century and converted the local population to Christianity, and the two village churches, though they failed to impress Cagliostro, are worth a visit. The Pieve was built in the ninth century, with material salvaged from a Roman temple to Jupiter, by Byzantine-influenced architects from Ravenna. Sunk into the ground behind the church is a sixth-century chapel founded by and later dedicated to St Leo, whose body lay here until 1014 when Henry II, Emperor of Germany, calling in at the town on his way home from defeating the Greeks and Saracens in Rome, decided to remove it to Germany. His plans were thwarted by the horses bearing the saint’s body – after a short distance they refused to go any further, so St Leo’s body was left in the small village of Voghenza near Ferrara. The heavy lid of the sarcophagus remains in San Leo’s twelfth-century Duomo, dedicated to the saint.

Travel offers; book through Rough Guides

Italy features

The latest articles, galleries, quizzes and videos.

The 10 most beautiful places in Italy – as voted by you

The 10 most beautiful places in Italy – as voted by you

Is there anywhere in the world as easy on the eye as Italy? From art-filled cities to heart-stopping coastlines via gorgeous landscapes, you could criss-cross t…

07 Dec 2016 • Natasha Foges camera_alt Gallery
An expert’s guide: where to stay in Venice

An expert’s guide: where to stay in Venice

Venice has been depicted and described so often that on arriving in the city you might have the slightly anticlimactic feeling that everything looks exactly as …

14 Oct 2016 • Rough Guides Editors insert_drive_file Article
7 highlights that make Genoa Italy’s most delicious city

7 highlights that make Genoa Italy’s most delicious city

Genoa is way off most travellers’ itineraries, but it’s time this northern Italian beauty – and its outstanding local cuisine – gets the recognition it …

10 Aug 2016 • Natasha Foges insert_drive_file Article
View more featureschevron_right

Join over 60,000 subscribers and get travel tips, competitions and more every month

Join over 60,000 subscribers and get travel tips, competitions and more every month