The town has been awarded an Orange Flag by the Italian Touring Club.
Built on the rocky outcrops of Rupe and Roccione that stand 629 metres above sea level, it still retains its mediaeval structure. It owes its urban layout to the union of two castles; Billi on Rupe and Penna on Roccione. Of ancient origins, it was inhabited by the Umbrians, Etruscans and Romans and developed around 1000, with the addition of fortifications, defences and religious buildings that created a delightful old town. It was a feud of the lords of Carpegna, before passing to the Malatesta of whom it claims to be the “cradle” - a fact hotly disputed by Verucchio. After the fall of Sigismondo Pandolfo Malatesta, here too Federico da Montefeltro came to power.
Around 1300 the two independent municipalities of Penna and Billi united in a single entity, as can be seen in the municipal coat of arms that shows two towers with the eagle of the Montefeltro. In 1572 the seat of the diocese of Montefeltro, now San Marino-Montefeltro, was transferred here from San Leo by Gregory XIII; a presence that still heavily influences the small town from both a social and urban point of view. Proof of this is provided by its magnificent cathedral, the Sanctuary of the Madonna delle Grazie and the Convent of the Augustinian Sisters.
The natural environment is characterized by Sasso Simone and Simoncello Park, part of which is in this territory. Vestiges of the past and the monumental and artistic heritage of the town and nearby villages create a prestigious cultural itinerary. Further proof of this are the numerous cultural events and shows held year round like the National Antiques Fair in July and International Street Art Festival in June. It also has several museums like “A. Bergamaschi” Diocesan Museum of the Montefeltro, Mateureka Calculus Museum, the Museum of Sasso Simone and Simoncello Park, the World of Tonino Guerra and The Places of the Soul, dedicated to the poet whose unusual creations can be found in Pennabilli and nearby and create a bizarre yet evocative poetic itinerary.