The cloister is the atrium of the chapel of the Fellowship of the Disciples of St John the Baptist "the Barefoot" and founded in 1376, was designed by Giuliano da Sangallo. Entirely frescoed by Andrea del Sarto and Franciabigio, it preserves one of the most important cycles of early 16th-century Florentine painting. Above the entrance door, after the restoration of the entire façade, shines a glazed terracotta lunette, attributed to Giovanni della Robbia, depicting St John the Baptist on a blue field dressed in camel skin and a gold cross, accompanied by two brethren of the company, depicted with the cilice in their hands and wearing the black tunic worn for religious ceremonies. Divided into slender columns with Corinthian-style capitals, the small cloister was decorated by Andrea del Sarto between 1509 and 1526 with the Stories of St John the Baptist and the four virtues (Faith, Hope, Charity and Justice) on the sides of the entrance doors. Giorgio Vasari mentions the commission for the frescoes in his 'Lives': "It was the custom in Florence to meet at the end of the Via Larga above the houses of the Magnifico Ottaviano de' Medici, opposite the garden of San Marco, the men of the Fellowship known as the Barefoot, named after St John the Baptist, which had been walled up in those days by many Florentine craftsmen, who among other things had made a courtyard of first-rate walls that rested on some not very large columns, When some of them saw that Andrea was becoming an excellent painter, they decided, as they were richer in spirit than in money, that he should paint around the aforesaid cloister twelve frescoes in chiaroscuro, that is, in terracotta, twelve stories from the life of Saint John the Baptist."
The work was executed with the elegant monochrome technique, a chiaroscuro without colours, depicting in eight scenes the vicissitudes of the saint, patron saint of Florence, from his birth to the famous dance of Salome and his beheading, from the baptism of Jesus to his preaching in the desert. Andrea del Sarto, a member of the confraternity, perfectly rendered the lifestyle, based on a sober and essential spirituality, through his frescoes.