A huge pointed rocky crest surrounded by rocks descending sheer into the hills of Romagna’s Apennines which gently slope to the Adriatic Sea; ancient buildings crowding the space between the superb fortress and the enchanting bell tower; the intertwining of history and legend, sacred and profane, between horrid prisons and inspiring parish churches: all of that can be found in San Leo. It was a height sacred to the Gods when Saint Leo got there, in the III century. He immediately thought it could be an ideal place for the diffusion of Christianity, and, in fact, it did, as this religion spread throughout the region and San Leo came to be known as the Montefeltro Diocese, after the ancient name of the village.
In the turbulent cycle of wars between Goths and Byzantines, Lombards and Franks, San Leo’s fame for the impregnability of its fortress spread around. In 963 Berengarius II, who had fled up here, elevated San Leo to capital of the Italic Reign. The town was besieged for several months by Otto I, the German emperor. Around 1200 AD the signory of the Counts of Montefeltro started spreading from here and eventually they settled their court in Urbino, with the title of dukes, where they had a prominent role in the development of Renaissance. Meanwhile, San Leo’s fortress was enlarged and embellished, especially thanks to Francesco di Giorgio Martini, the architect working for the Dukes of Montefeltro. P. Bembo defined it as a “superb war tool”. San Leo’s political and military importance definitely declined in 1631, following the fate of the Dukes of Montefeltro. Its territory fell under the rule of the Papal State and the fortress was turned into a prison.
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Rimini Itineraries 
