Pennabilli is a “magical” place. The Dalai Lama stopped here twice, and internationally-renowned artists such as Michelangelo Antonioni and Ezra Pound also passed through the town.

Built on the rocky ledges of the Rupe and the Roccione, the town is faithful to its medieval layout and owes its current urban layout to the union of the two castles: Billi, above the Rupe, and Penna, on the Roccione. 

Having very ancient origins, it has seen the Umbri, the Etruscans and the Romans succeed to one another. It was the feud of the Lords of Carpegna before passing to the Malatesta family of which it claims to be the “cradle”–a fact disputed with Verucchio.

Around 1300 the two autonomous municipalities of Penna and Billi merged giving rise to a single entity, as depicted in the civic coat of arms: two towers with a feltresca eagle.

In 1572 Gregory XIII transferred the seat of the Diocese of Montefeltro from San Leo to here–a presence that still strongly characterises the town both from a social and urban point of view. The Cathedral, the Sanctuary of the Madonna delle Grazie, the Convent of the Augustinians, places of strong appeal, bear witness to this, together with its natural environment, characterised by the presence of the Sasso Simone and Simoncello Park.

The numerous testimonies of the past, the monumental and artistic heritage present in the historic centre and the villages, create a prestigious cultural path, highlighted also by countless cultural events and performances throughout the year, such as the “National Antiques Market Exhibition” in July and the “International Street Art Festival” in June.

There are several museums: the “A. Bergamaschi” Diocesan Museum of Montefeltro, the Mateureka Calculus Museum, the Sasso Simone and Simoncello Park Museum. Tonino Guerra, poet, writer and world-famous screenwriter, had a close relationship with Federico Fellini, as a friend and collaborator. He lived in Pennabili for most of his life, as testified by the museum.

“Il Mondo di Tonino Guerra” (The World of Tonino Guerra) and “Luoghi dell’anima” (Places of the Soul)–an extensive museum composed of seven installations that characterise a bizarre and captivating poetic journey.

Pennabilli has been awarded the Orange flag by the Italian Touring Club.