Between history and legend
The best way to enter Tolentino is through the Porta del Diavolo (Devil’s Gate), a 13th-century entrance surrounded by well-preserved walls leading to the Ponte del Diavolo bridge. According to legend, the person in charge of building it asked for help from Satan, who, in return, demanded the soul of the first person to cross it. But the builder was smarter and let a small dog go first.
The centre of Tolentino, in the heart of the province of Macerata, is a succession of gems. Don’t miss the Cathedral, the Art Nouveau-style Palazzo Politeama, the Basilica of San Nicola with its splendid wooden coffered ceiling, and the unique MIUMOR (International Museum of Humour in Art and Caricature).
Outside the village you can discover other pearls of the Le Marche hinterland. At the Rancia Castle you can retrace the history of the Compagnia della Rancia, a Tolentino-based theatre company that caught Italy’s imagination with famous musicals. To combine culture and nature, we recommend visiting the Fiastra Abbey and its green gardens.