The Comune di San Leo describes their town as 'a sharp pinnacle surrounded by overhanging cliffs in a countryside sloping from the Appennines to the sea, with houses clustered between a magnificent fortress and a prominent bell tower'. It looks even more spectacular in real life.
San Leo is a real hill top town. It came under control of the Montefeltro family from the 14th century. They also ruled Urbino and they commissioned Francesco di Giorgio Martini, architect of the Dukes of Urbino, to enlarge and enrich the fortifications.
It was so well done that when San Leo fell into the hands of the Church the castle was turned into a prison. The cells can still be visited and the view from the top must have been frustrating consolation for those unfortunate to be incarcerated there.
Other buildings of note are the Francescan Convent of Sant'Igna, the Parish Church and the 'Torre Campanaria' or watchtower.
The cliff top is a precipitous 630m cliff and one the most impressive sights in the region.
It was here Cagliostro was imprisoned until his death for being a masonic member and was the symbol of the power of the Montefeltro family.