Pennabilli is a delightful, age-old town where you immediately notice the strong, lively and friendly character of the people.

The religious capital of Montefeltro and the seat of the bishop of the Diocese of San Marino-Montefeltro, Pennabili is situated on the western side of Mount Carpegna which slopes down to River Marecchia. It was during the Middle Ages that the history of Pennabili took the decisive turn that made it what it is today. About 1000 AD, two separate castles were built: that of Billi, on the Rupe, and that of Penna, on the Roccione; these were the sites of two autonomous municipalities which merged in 1350 to create the municipal entity of Pennabili.

The medieval layout of the streets and alleys of Pennabili was formed after the union of the municipalities. Over the centuries, Pennabilli was highly contested and ruled in turn by the Malatesta, the Montefeltro, the Medici and the Papal State. In 1572, with the transfer of the “sede viscovile” (bishop’s headquarters) from San Leo, Pope Gregory XIII declared it a “city”. The importance of the presence of the diocese is apparent in the various buildings and institutions of a religious nature found in the city, from the Cathedral to Santuario di Sant’Agostino (The Sanctuary of St Augustine) with the monument of Madonna delle Grazie (Our Lady of Graces), the Convento delle Agostiniane (Convent of the Augustinians), the Chiesa e l’Ospedale della Misericordia (Della Misericordia Church and Hospital) the beauty of which remains intact. The city as we know it now features many attractions and places of interest, with its Museo diffuso dei Luoghi dell’anima di Tonino Guerra (Eco-museum of the Places of the Soul of Tonino Guerra), its sculptures, and the extraordinary Mateureka, Museo dell’informatica e del calcolo (Mateureka, Museum of computation and calculation) which proposes a whole new approach to mathematics; while the spiritual dimension also encompasses the Museo diocesano (Diocesan Museum) which houses various important works of religious art. Of no less interest are the villages of great natural beauty around Pennabilli which can be explored by car or, if you feel more enterprising, by bike.

There are panoramic areas like the Castello di Bascio (Bascio Castle) or Miratoio, or the Trabocchetto Pass, a fantastic place to go hiking or mountain biking, as are also the Parco del Sasso Simone e Simoncello (Park of Sasso Simone and Simoncello) at the entrance to which is the Museo del Parco naturale (Museum of the Nature Park), or indeed Lago di Andreuccio (Lake Andreuccio) at Soanne. There are two special occasions on which to visit Pennabilli: the Busker Festival, held every year in July since 1970, and the Mostra dell’Antiquariato (Antiques Festival) at Palazzo Olivieri, one of the oldest and finest in Italy.

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