Pennabilli is a medieval town, capital of the southernmost municipality of Emilia Romagna. Its territory is partly covered by the Regional Park of Sasso Simone and Simoncello. Despite its small size, the town has had various important people, who have enriched the city's culture. Particularly important are Matteo da Bascio (born Matteo Serafini), founder of the Frati Minori Cappuccini clerical order; Orazio Olivieri, a priest who went on a clerical mission to Lhasa and contributed to the first Italian-to-Tibetan dictionary (which was then used as based for the first English-to-Tibetan); and Tonino Guerra, a poet who has lived in Pennabilli since 1989.
Del castrum Bascii o Biscii, in origine di pertinenza degli Olivi di Pignano, si ha notizia sin dal 1145, citato fra le terre confermate da Papa Eugenio III al monastero Camaldolese di San Salvatore di Monte Acuto.