This complex rises on the “hill of Paradise,” outside of the primitive enclosing town walls, where the S. Salvatore Church was built in 1114. After having assumed the title of San Leonardo, halfway through the thirteenth century, the church was passed to the Franciscans, who built a convent and a small cloister. In 1606, a steeple was created, with a characteristic inclination, while the construction of the present cloister continued from 1611 to 1627.
The façade, characterized by a double mullioned window surmounted by a rose window, is made of a local grey sandstone. Above the portal, there is a lunette with a high-relief representation of Saint Francis, a piece made by the local sculptor, Antonio Brogi, who also made the Via Crucis inside of the church. The glass windows were made by Antonio dell’Alvernia and Francesco da Terranova in 1479. The internal plan has a simplicity typical of the architecture of mendicant orders: only one nave with a brief transept, characterized by one central chapel and two lateral chapels.
Among the pieces of art preserved inside of this church are la Crofissione by Francesco Morandini, otherwise called il Poppi (1544-1597), la Madonna con Bambino e Santi (1548) by Vasari, La vocazione di S. Matteo by Salvi Castellucci, a Crucifix (17th century) by Giovanni Patriarchi, Cristo nell’orto (1652) by Sallustio Lambardi. The church also preserves a valuable organ from the mid 16th century and a cantoria from 1546 made of sculpted stone. In the small space that brings you from the vestry to the cloister, there is a fragment of a fresco representing Maria che allatta Gesù e due Santi made by one of Spinello Aretino’s apprentices.
The rectangular-shaped cloister is characterized by a double Tuscan-style loggia. Its original construction dates back to the 12th century. The side opposite the entrance shows the coat of arms of the friars. The 1627 frescoes on the lunettes are by Pelliccione da Colle. They represent the Scene della vita di S. Francesco and were commissioned by the most important Castiglion families.