SAN LEO

Right in the heart of the Montefeltro, on a rocky shelf, lies San Leo, which dominates the Marecchia valley. It is a place exceptionally well-protected by nature itself, and has a fascinating military and religious history, in which many episodes of hard battles mingle with far-reaching mystical events. San Leo was inhabited by the Umbro-Sabelli tribes, by the Gauls and by the Romans, and was the cradle of Christianity as it spread over the whole area. It was the first land to be given as a vicariate to the Montefeltro family, who took the name of this estate and who would always keep the imperial eagle in their coat-of-arms.
Like all forts and all churches, those of San Leo, too, are real history books, which tell of constant conquests and new cults, which superimpose themselves on ancient ones.

A brief look throughthe political events of the Terra del Duca is sufficient to make one realise the importance given to the possession of this land by the powers that succeeded to it one after another over the centuries.

It was the first “capital” of the Montefeltro family, with the legendary Montefeltrano I (1135-1202) extending his dominion to the “Comitato” of Urbino, Pesaro and Rimini, and lost its role when Federico II of Svevia gave Urbino (to which the counts would move in 1234) to Buonconte and Taddeo da Montefeltro in 1226.
After a very brief republican period, San Leo passed into the hands of Counts Guido and Nerio Di Petrella (or Della Faggiola); it came back to Montefeltro with Count Nolfo, who had to surrender it to the Church. Then the Malatesta became its overlords and it was taken from them to be given to Federico da Montefeltro in 1441.
During the period of rule by the great Federico, Francesco di Giorgio Martini extended the splendid Fort, which seems to melt into the rock it stands on. Quoted by Machiavelli in “The Art of War”, it was defined by Pietro Bembo as” “The most beautiful and the largest instrument of war in the region”. 

It was twice conquered by Cesare Borgia, and twice, he was driven out of it: it was returned to Della Rovere but was conquered, together with all the Dukedom, by Lorenzino dei Medici, then returning to the dominion of Della Rovere. Stories of war, of victories and defeats.
The Medici Palace and the Della Rovere Palace remain to testify to these, serving to accommodate visiting lords, but they were also signs of their power. The Fort, transformed into a prison by the papal government, accommodated Felice Orsini, Napoleon III’s assailant, in 1844 and many liberals from the Romagna region, but the most famous of its prisoners was without doubt the legendary Cagliostro, who died there in 1795.