Clamped to the summit of a dizzying precipice, the beautiful fortress of SAN LEO has only been part of Emilia-Romagna since 2006, when the town and five others voted in a referendum to leave Le Marche and join its northern neighbour. Generations have admired the fortress – Machiavelli praised it, Dante modelled the terrain of his Purgatory on it, and Pietro Bembo considered it Italy’s “most beautiful implement of war”.

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 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 trapdoor 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. Cagliostro eventually died of an apoplectic attack, unrepentant after four years of being virtually buried alive.

Book through Rough Guides’ trusted travel partners

Italy features

The latest articles, galleries, quizzes and videos.

19 places to get utterly lost

19 places to get utterly lost

One of the great joys of travelling is stumbling across unexpected places, wandering without a single destination in mind and embracing the journey. These place…

12 Sep 2017 • Keith Drew camera_alt Gallery
The most beautiful country in the world – as voted by you

The most beautiful country in the world – as voted by you

There's nothing like an amazing view to inspire you to book your next trip, whether you're drawn by rolling countryside, isolated islands or soaring mountain …

30 Aug 2017 • Rough Guides Editors camera_alt Gallery
Where to find the best beaches in Italy

Where to find the best beaches in Italy

From secluded coves to lively seafronts, there are plenty of places to sun worship in Italy. But with an increasing number of hotels charging for access to the …

20 Jul 2017 • Rough Guides Editors insert_drive_file Article
View more featureschevron_right

Weekly newsletter

Sign up now for travel inspiration, discounts and competitions

Sign up now and get 20% off any ebook