A wealth of history, legends and charm in the medieval villages of Romagna

A short drive from San Marino and from the famous Riviera, the Romagna hinterland offers a landscape with an abundance of fascinating fortresses. Years of history and architectural beauty await beneath the vast, open sky. Tiny, ancient medieval villages are home to mystery and charm preserved for millennia. 

With so much to choose from, let us suggest a few destinations to help you explore the epic Middle Ages.

Sant’Agata Feltria

Famous as the home of the prized white truffle, Sant’Agata Feltria is a true storybook fortified village boasting a fairy-tale castle and numerous mystical places, including sanctuaries and convents! Located in the Montefeltro hills between the valleys of the Savio and Marecchia rivers, the village’s historical centre features the Route of the Fountains, created by the mosaicist Marco Bravura and that includes the Fountain of the Snail, based on an idea of the poet Tonino Guerra.

Author: Photographic Archive Province of Rimini

San Leo

Straddling the Marche and Romagna regions, San Leo is part of the I Borghi più belli d’Italia (the prettiest villages in Italy) association thanks to its marvellous panoramic location in the heart of Montefeltro. The village is dominated by the imposing Rocca, one of the most significant military constructions of its time and among the best preserved in Italy, and features a host of magnificent architectural treasures.

Author: Photographic Archive Province of Rimini


One of the most beautiful and most famous villages of Emilia-Romagna, Sant’Arcangelo offers a wealth of sacred and profane jewels dating back to ancient times. Some of the most famous are the Rocca Malatestiana, the Castle of Paolo and Francesca, the Torre del Campanone (the bell tower) and the church of San Michele Arcangelo. Over the centuries, Sant’Arcangelo has been home to artists and intellectuals, poets and actors (possibly also Pope Clement XIV).

Author: Photographic Archive Province of Rimini


The village overlooks the Marecchia river in the heart of a majestic natural amphitheatre at 630 metres above sea level in the Alta Valmarecchia. Pennabilli is rich in ancient history and boasts fabulous and primordial natural and environmental panoramas. Its prestigious cultural route presents numerous testimonies from the past, as well as the monumental and artistic heritage in the historical centre and in the hamlets. 

Author: Paritani


Home of the powerful Malatesta family, the town features ancient winding streets, three squares with imposing palaces and medieval walls punctuated by towers offering a breath-taking view of the Valmarecchia and the Adriatic coast. Gates in the wall still mark the entrance to the citadel. 

Author: Paritani


Located between the valleys of the Conca and Foglia rivers, Montegridolfo was a stronghold of the Malatesta family. This small jewel is brimming with centuries of history, and is dotted with laurel bushes, olive groves and vineyards. Be sure to visit the Castle and the Cagnacci fresco in the Church of San Rocco. The Museum of the Gothic Line, bearing witness to World War II, and the shelters are worth a visit.

Author: Mosconi


Famous for the “medieval festivals” held in June each year, Brisighella is a romantic town located in the province of Ravenna. This medieval town is perched atop three rocky pinnacles: the first is home to the Rocca Manfrediana, the second to the Sanctuary of Monticino and the third to the Clock Tower. Immersed in a lovely hilly landscape, Brisighella is part of the I Borghi più belli d’Italia association. 

Montefiore Conca

È lo stereotipo del borgo medioevale: una possente rocca con le sue torri, un imponente complesso militare, un dedalo di viuzze, un villaggio fortificato, una Montefiore Conca is the stereotypical medieval village with a mighty fortress with towers, an imposing military complex, a maze of narrow streets, a fortified village, an impressive square fort, ancient city walls, palaces, churches and monasteries whose ruins and remains can still be visited today. 

Its monuments and palaces reflect the town’s splendour, telling tales of centuries past.

Author: Paritani


Belonging to lands of the Malatesta Montescudo family, Montescudo abounds with archaeological evidence linked to centuries of clay and terracotta production. Ceramics are still made by hand here today. This beautiful village’s gems include the city walls, the 14th-century Civic Tower, a unique icehouse and numerous farmhouses and rural villages throughout the countryside!

Autor: Paritani

Photographic Archive Province of Rimini