The pride of the itinerary across the castles of Upper Valmarecchia is the wonderful medieval village of San Leo, which is one of the most beautiful historic towns in Italy. The other resorts of this itinerary are all situated a short distance from San Leo, and distribute both right and left of Valmarecchia and around the picturesque city of Novafeltria.

San Leo is a picturesque village of great fascination. It rises on the top of an impressive rock spur, and still retains its exceptional medieval and Renaissance architectural patterns. In the X century,  San Leo was appointed capital of the Kingdom of Italy by Berengar II, who chose it for its imposing military fortifications.

The city centre is dominated by the impressive rock, which is one of the most beautiful Renaissance fortresses in Italy. Built in the Early Middle Ages, it was subsequently remodelled in the fifteenth century by Federico da Montefeltro Duke of Urbino, who commisioned the restoration works to one of the most illustrious military architects of those times, Francesco di Giorgio Martini. Today, visitors will have the opportunity to admire the enchanting courtyards and bulwarks of the structure. The wide inner halls are now the seat of an interesting exhibition gathering ancient weapons and memorabilia. Not to be missed is the famous cell of Cagliostro, a notorious magician, mason and alchemist who lived there in the eighteenth century.

Those flocking to San Leo won't miss the opportunity to visit its enchanting old town, which is peppered with outstanding monuments and buildings. Piazza Dante is crowned by the wonderful medieval parish church, XII-century Duomo and Palazzo Mediceo. The Parish Church cherishes the famous ciborium of Duke Orso, who dates back to the IX century.

Sant’Agata Feltria, a picturesque medieval village which is dominated by an impressive castle, is situated a short distance from San Leo, and can be reached from there crossing the River Marecchia. Like the castle of San Leo, Fregoso Fortress underwent extensive restoration works commissioned by Federico da Montefeltro.

Tourists will have the possibility to enjoy breathtaking views over the underlying landscapes, as well as to visit the major attractions of the castle, such as the adjoining sixteenth-century frescoed chapel and the inner historical museum.  

Petrella Guidi and Talamello develop amidst the sweet hills that flank Valmarecchia, and are situated a short distance from Novafeltria. Even if they are not real castles, they both boast an impressive fortified layout. 

Talamello, which rises on the top of an impressive rock spur overlooking Novafeltria, boasts a lovely old town and enchanting landscapes. Petrella Guidi is one of the best preserved medieval villages of Romagna, what makes this intimate historic town an architectural jewel of rare beauty.

Crossing the river Marecchia, tourists will have the possibility to reach the ruins of Maiolo Castle. This is the ideal destination for the lovers of hiking, since it is surrounded by steep slopes and thick woods. Maiolo, Castle which once was one of the most important fortresses of the surrounding area, suddenly collapsed during a May night of the eighteenth century. Only two towers withstood, and still boast breathtaking views over the underlying landscapes.