San Leo is in the heart of the Montefeltro countryside to the south-west of Rimini, and on a hilltop 600 metres above sea level that has been occupied since Roman times. San Leo is listed as one of the 'most beautiful villages in Italy' and also has the Orange Flag award for sustainable tourism.
The highlight of San Leo is the stunningly located castle, on a large craggy rock above the village (or rather a precipitous cliff, on one side) - and very well worth the short steep climb from the village. It even impressed Dante, who based his descriptions of purgatory on the site.
Begin a visit to San Leo at Piazza Dante, home to the most important religious and civic buildings of the city. Among the religious buildings are the Parish Church, the oldest church (7th-9th century) in the city and with stone-work reinforced by powerful buttresses. The interior is divided into three naves by columns and pilasters, and united by the clever use of the arcades.
The church contains two works of particular importance: the ciborium, which was donated by Duke Orso (882), Governor of the city, and the so-called "Sacello" (Chapel), built by Saint Leo in the 4th century (home to the remains of Saint Leo until Henry II ordered them to be taken to Germany, where they became lost).
In the same square stands San Leo Cathedral (12th-13th century) in the Lombard-Romanesque style. Also built with sandstone it stands on the site of an older church.
There is no façade, given its location on the edge of the cliff of St. Leo, and access is from a portal on the side of the cathedral which is surmounted by busts of St. Leo and St. Valentine.
The cathedral has the form of a Latin cross, with two aisles divided by columns forming seven arches on each side. In the Presbytery there is a large crucifix which is a copy of the one that the Count of Montefeltro gave the church in 1205.
A few metres from the Duomo of San Leo is the Watchtower (12th century) built in sandstone with an exterior in the shape of a box while the inside is circular. Initially used as a watchtower, it was later transformed into a bell tower, and there is a bell dating from the fourteenth century.
The Palazzo Medici now houses the San Leo Museum of Sacred Art, with artefacts of sacred art from the 8th to the 18th century, as made for altars and rooms of monasteries. The museum tour begins at the Lapidary, which welcomes the city's ancient sculptural artefacts (VIII - XIII century). Among the most important are the remains of three limestone arches, richly decorated, which made up the tabernacle of the early medieval cathedral, and four fragments of the Carolingian church of the presbytery enclosure.
The "Room of the painted panels" represents the earliest pictorial history of the city and contains the oldest artefacts: a crucifix from the 14th century; a painting of the "Madonna with the Apple" by Catarino di Marco from Venice (c.1375) and a 15th century tableau by Luca Frosino depicting the "Madonna and Child". The third room is dedicated to the 16th century, with numerous paintings, largely due to the Council of Trent which renewed the furnishings and pictures in the church buildings. Among the works, note "Santa Rita da Cascia" by Giovan Francesco Guerrieri (1636) and the "Deposition" by Giovanni Francesco Barbieri, called the "Guercino" (1591-1666).
Among the civil buildings of interest in San Leo is the 16th century Palazzo Medici, initiated by the Della Rovere and then continued by the Medici, between 1517 and 1523 following the capture of the city by Florence.
The internal structure of the building follows a Renaissance plan, organized around the reception rooms of the ground floor, while the façade, in addition to the elegant stone profiles of the windows, has the characteristic portal with the coat of arms with the lily of Florence and Pope Julius II della Rovere (1443-1513).
Continuing out San Leo visit, the 17th century Della Rovere Palace built by Francesco Maria II della Rovere is very beautiful with an elegant late 16th century façade animated by the portal and windows, and surmounted by gables in the 'Tuscan Mannerist' style.
The Palazzo of the Counts of Nardini is believed to have an original core dating back to the thirteenth century - in subsequent periods, however, it was expanded and transformed until the late Renaissance, and is now severe and unadorned except for four portals with an arch.
Leaving along Via Leopardi we come to the Fort at San Leo. From the Middle Ages onwards the area surrounding the fortress was used for strategic and defensive purposes, but its current design and appearance date to the second half of the 15th century when Federico da Montefeltro (1422-1482) put in place various works, under the supervision of the architect Francesco di Giorgio Martini (1439-1501).
The structure of the fortress is divided into two distinct levels: at the top stands the impressive tower with an elongated shape while below two linked towers complement the building. The fort has decorative motifs such as cornices and corbels.
The fortress housed many people of great importance, including Dante (1265-1321), the Count of Cagliostro (1743-1793), who was a prisoner of the Papal States here, and St. Francis (1182 ca.-1226), who, it was said, was the founder of the Convent of St. Igne, nestling in the countryside one mile from Saint Leo.
(See also a detailed guide to the history of the name San Leo at history of San Leo.)
The traditional cuisine of the Marche region is simple, with rustic soups such as one made with vegetables, meatballs, chicken livers, sausages and sliced bread. And if you find that difficult to digest, try a few sips of the digestive system known as "Balm of Cagliostro", named after the imprisoned Count of Cagliostro here in San Leo, who it is said invented the liquor.