This spectacularly sited hilltop monastery is carved into the rock over the cave where St Benedict supposedly spent three years meditating. As well as its setting, described by Petrarch as ‘the edge of Paradise’, it boasts an interior almost entirely covered in 13th- to 15th-century frescoes. The Chiesa Superiore (Upper Church) features works by the 14th-century Sienese school and later 15th-century works illustrating episodes from the life of Benedict. Downstairs, the Chiesa Inferiore (Lower Church) has works from the 13th-century Roman school.
Accessible from the lower church, the Grotta di San Benedetto is in better shape now than when Benedict, here represented by Antonio Raggi's delicate marble statue, did his time here in around AD 500.
Another highlight is a painting of St Francis in the Capella di San Gregorio. This is reckoned to be one of the earliest known depictions of the saint, who is portrayed standing up and without his stigmata. This, scholars reckon, dates the painting to some time before 1224, the year St Francis supposedly received the stigmata.