This is the place where St Francis, going from la Verna to Assisi, is said to have planted a wooden cross in the ground. The church and monastery were built between 1499 and 1534, and the interior features artworks from the late 16th and 17th century. The coat of arms over the entrance door is that of the Fraternita di Santa Maria del Borghetto, an old charitable brotherhood which was based in Piazza Mameli. This church is particularly important for the community as it is where Lorenzo Taglieschi, a major chronicler from the 17th century, is buried.
The distinctive feature of the castle is the cylindrical tower on its corner. The Castello di Montauto, together with villa La Barbolana and Castello di Galbino, was one of the residences of the old Galbino family. Here Francis of Assisi, not yet a saint, is said to have rested for a few days, after he had received the stigmata at La Verna in 1224. While here, Count Alberto gave Francis a new priest's habit in exchange for the old, stained one. This was soon considered a precious relic and was kept in the castle’s chapel until 1502 when the Florentines brought it to Florence. The habit of Montauto is now displayed in the Santuario della Verna.
The 16th century convent was built at the same time as the villa La Barbolana. Originally it was a Franciscan convent that was intended to assert the Galbino family’s relationship with St Francis of Assisi, who had been welcomed in the castle of Montauto after receiving the stigmata in La Verna. It was probably Federigo Barbolani, the founder of both the villa and the convent, who wanted to consecrate this place by planting a tree that grew from an acorn from St Francis’ holm oak near Siena.