Overlooking the square of the same name in Castiglion Fiorentino, the Church of St. Francis (San Francesco) was built by the Franciscans in the mid-13th century on pre-existing structures, dedicated to San Salvatore e San Leonardo. The building has a Romanesque-Gothic sandstone facade, and on the portal lunette you can admire a recent terracotta depicting St. Francis instructing the turtledoves, the work of Antonio Brogi, a local ceramist.
The layout, according to Franciscan custom, has a single nave concluded by a short transept with three cross-vaulted chapels and a gabled roof.
Inside are kept valuable works, such as the 1548 panel painting representing The Virgin with St. Anne, St. Anthony and St. Sylvester (La Vergine con Sant’Anna, Sant’Antonio e San Silvestro) by Giorgio Vasari, whose preparatory drawing is kept in the Louvre in Paris; The Crucifixion (La Crocifissione) by Francesco Morandini, known as Il Poppi; and The Vocation of St. Matthew and Announcement of the Angel to St. Anne (Vocazione di San Matteo e Annuncio dell’Angelo a Sant’Anna) by Salvi Castellucci.
Also of note are the wooden Crucifix painted in faux bronze by Giovanni Patriarchi and a wooden statue representing Christ caught in the Garden of Gethsemane, carved by Sallustio Lambardi of Lucignano in 1651, which is carried in procession on Holy Tuesday by the confraternity of St. Anthony (Sant’Antonio).
To the left of the church is a rectangular-plan cloister, rebuilt in the early decades of the 17th century on a 13th-century portico. Under the arches are frescoed lunettes with scenes from the life of St. Francis, by Giovanni Pelliccioni from Colle Val d’Elsa.
On the right side of the church, in 1560, was built the oratory of the Confraternity of St. Joseph (San Giuseppe); which today belongs to private owners.