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The most famous of Tuscany’s rural monasteries might also be the loveliest, set in the scarred hills of the Crete Senesi northeast of Montalcino and surrounded by glorious scenery that could easily inspire religious fervor. Founded in 1313 by a group of wealthy Sienese businessmen who wanted to devote themselves to the contemplative life, the red-brick monastic complex was built in the early 15th century. The Olivetans, still an active order within the Benedictines, were trying to restore some of the original simplicity and charity of the Benedictine rule, and the monks cared for victims during the 1340s Black Death. What draws most visitors today is the 36-scene fresco cycle by Luca Signorelli and Sodoma illustrating the Life of St. Benedict, one of the masterpieces of High Renaissance narrative painting and Sodoma's greatest work. After parking, walk under the gate tower with its small cafe and through the cool woods for about 5 minutes to the bulky brick heart of the complex. The entrance to the monastery is around to the right: A signed doorway leads into the Chiostro Grande.

Signorelli started the job here in 1497. He finished nine of the scenes before skipping town the next year to work on Orvieto's Duomo, where he created his masterpiece, a Last Judgment . Antonio Bazzi arrived in 1505 and finished the cycle by 1508. Bazzi is better known as "Il Sodoma," a derogatory nickname that is probably a reference to his predilection for young men. Sodoma was married at least three times, however, and may have had in the neighborhood of 30 children. You’ll meet this eccentric character in scene 3, in which Benedict asks God to mend a broken earthenware sieve belonging to a poor woman and his prayers are answered—proof that God works his wonders in small ways. Sodoma incorporates a self-portrait into the scene, and appears with his flowing black hair, garbed in the fancy clothing that a nobleman had shed upon entering the abbey; he’s accompanied by his two pet badgers, a chicken, and a tamed raven.

To follow the cycle's narrative, start in the back-left corner as you enter, with a scene of the young Benedict, astride a spirited white horse, leaving his parents’ home to study in Rome. The scenes are especially appealing because of the precise details they provide of medieval life: In scene 11, showing Benedict founding monasteries, is a visual primer of medieval construction techniques: A workman atop scaffolding trowels plaster onto brick vaulting while a cohort applies whitewash with a brush on a long pole and a stonemason prepares the base of a column. Scene 19 shows Benedict sending away harlots that Florenzo, an evil monk, had smuggled into the monastery to tempt the brothers; allegedly, Sodoma painted the women in the nude for verisimilitude, but the abbot was so incensed that he made the artist put dresses on them. (Signorelli depicts Florenzo’s death in scene 21.) In scene 6, Sodoma compresses several episodes of an act of mercy into one image, as he shows a priest taking bread out of the oven in the background, Christ appearing to him a vision (shown in a medallion) to tell him to share it with the hermit Benedict, the priest recoiling from the vision on the right, and enjoying a meal with Benedict on the left. Signorelli shows us Benedict Receiving Mauro and Placido, depicting the arrival of two young boys of noble birth sent to Benedict to live a monastic life; one day when Placido began to drown in a lake, Mauro miraculously walked across the surface of the water to save him, and the two eventually spread the Benedictine order to far-flung corners of Europe. Inside the church are gorgeous choir stalls that Giovanni da Verona (1505), a monk who was trained in the art of woodcarving, crafted in intarsia, showing some riveting city scenes with remarkable perspective.