The Cloister of the Scalzo was part of the building designed for the Confraternity of St. John the Baptist, founded in 1376 and called "dello Scalzo" because the cross-bearers in the Confraternity's processions was barefooted.

The Brotherhood was suppressed in 1785 by Pietro Leopoldo of Lorraine, who sold off their property with the exception of the cloister containing sixteen frescoes in chiaroscuro, showing episodes of the Life of St. John the Baptist, painted by Andrea Del Sarto (1486-1530) (only two of the scenes were painted by Franciabigio (1482-1525), while Andrea was in Paris in 1518).

Painted between 1514 and 1524, the frescoes represent an extraordinary example of stylistic and technical perfection in the art of a Master, who played an important role in the complex artistic events of Florence at the beginning of the 16th century.
He played also a role now recognized as fundamental to the developement of Mannerism.