Back in the Middle Ages, a little tabernacle stood at the foot of the hilltown Castiglion Fiorentino: inside, it held an image of the Virgin and Child, attributed to Luca Signorelli. Once Cosimo I dei Medici had reconquered the area, his wife Eleonora di Toledo prayed before the image, and had a temple built to house it properly.
The first stone of the chiesa della Madonna della Consolazione (church of Our Lady of Consolation) was laid in 1565, and work continued for roughly enough forty years. The church is built upon an octagonal plan, and its exterior is interrupted about two-thirds of the way up by a wide ledge, which acts as a stylistic watermark. Below it, the church is Doric in style, with its rectangular windows built into niches; above it, an Ionic style predominates, punctured by large oculi. There is still no consensus as to who created this extraordinary work. Some detect the hand of Giorgio Vasari, others argue that Antonio da Sangallo submitted the designs.
Work was completed on the church in 1607; but only a year later, on the back of some Biblical rains, the dome caved in. The architects judged it better to replace it with a simple pyramidal roof. Inside, in one of the octagon's side chapels, an altar by Berrettini contains a fresco of the Madonna. On the morning of 9 June 1967 a bolt of lightning caused the roof to collapse again, and only 16 years later was the church reopened.