The abbey of Monteoliveto Maggiore which stands atop a spur of the Crete Senese, the barren, rocky country southeast of Siena, is one of the most important and best preserved monastic complexes in southern Tuscany. It was founded by the prominent and well-to-do legal scholar Giovanni Tolomei (1272-1348), who resigned his post as podestà of Siena and renounced his worldly interests to take up the life of a hermit. He was joined by two other men from Siena, Ambrogio Piccolomini, and Patrizio Patrizi. The three built themselves shelters in this hostile landscape and over the years still others were attracted to the fledgling ascetic community. On March 26, 1319, the Bishop of Arezzo, Guido Tarlati, confirmed the congregation as a new religious order.
The abbey is constructed entirely of brick and comprises a jumble of structures linked by three inner courtyards, or cloisters, of different sizes and with different functions. The Great Cloister (Chiostro Grande) around which the more important communal spaces are disposed was constructed in stages between 1426 and 1443. The cloister was frescoed by Luca Signorelli with nine scenes on the west side (1497-99) and Sodoma with twenty-eight scenes (1505-08 and after 1513). The fresco cycle is comprised of thirty-six Scenes from the Life of St Benedict; St Benedict Presenting the Rule to the Olivetans; Man of Sorrow; Christ Carrying the Cross.
The life of St Benedict is considered as a reflection and ideal of the monastic life. The exemplary nature of the scenes presented in the cloister at Monteoliveto Maggiore gives the impression that they were deliberately selected for their bearing on life within the monastery. Virtually all of the community's activities and concerns are reflected in them. The ultimate textual source for the Benedict cycle was the biography written by Gregory the Great in about 593-94, which tells the story of the important monastic founder in thirty-eight chapter.