The Chiostro dello Scalzo (Cloister of the Scalzo) is all that remains of a building once owned by a confraternity devoted to Saint John the Baptist and known as the Compagnia dello Scalzo. It was so named, for the leader of the confraternity would, as a sign of his humility, walk barefoot (scalzo) in its processions through the city.
The small cloister was originally the atrium to the chapel of the confraternity, which was founded in 1376. The relief in glazed terracotta (c. 1510), above the entrance, is by Giovanni della Robbia (1469-1529) and depicts St John the Baptist and two confratelli.
The walls of the cloister are decorated with a series of monochrome frescoes, most of which were painted between 1513 and 1526 by Andrea del Sarto (1486-1530). However, two of the frescoes were painted by his friend Franciabigio (1482-1525), while Andrea was working in France.
The cloister was originally covered with a simple wood and tile roof, which sloped towards the centre of the courtyard. In 1722 Pietro Giovannozzi radically altered the structure, vaulting the four sides of the portico and adding a second column at the corners for reinforcement. The newly created lunettes were painted by Giovanni Panaioti with mortuary symbols.