Surprisingly full of Renaissance masterpieces, the Val di Chiana retains in nearly all of its territory tangible signs of the fifteenth century Sienese culture. In the village of Sinalunga, we have two great examples of that culture, the first one, in the collegiate church, is the Madonna and Child enthroned with Saints Sebastian and Martin by Benvenuto di Giovanni and the second one, in the convent of San Bernardino by the same artist, the Annunciation signed and dated 1470 which represents one of the artist's most accomplished works for its refined chromatic range and a very careful spatial perception.
In the same convent two more paintings by Guidoccio Cozzarelli, the Baptism of Christ datable to around 1483 and the curved panel depicting the Coronation of the Virgin with Child and the Saints Simon and Thaddaeus, dated 1486. Montepulciano houses some of the most remarkable masterpieces of the Florentine Renaissance, source of inspiration for the subsequent works of classical figurative arts widespread in the Sienese region; such as the tombstone of the Poliziano humanist Bartolomeo Aragazzi, carved by Michelozzo, collaborator of Donatello, of which only a few fragments are left in the Cathedral of Santa Maria Assunta.
In the Civic Museum Della Robbia ceramics are displayed among which are the altarpiece of Madonna of Montecastello by Andrea della Robbia (1483-84) and the delicate Holy Family with the young Saint John by Sodoma. The church of Santa Lucia holds the beautiful Madonna and Child by Luca Signorelli, characterized by the rigorous spatial arrangement. Climax of the late-Renaissance architecture is the Temple of San Biagio, an imposing building whose construction was supported by Pope Leo X, born Giovanni Lorenzo de' Medici, disciple of Angelo Poliziano. It was completed in 1580.
In the Cathedral of Chiusi the late-Renaissance is represented by a beautiful panel by Girolamo di Benvenuto Madonna and Child Enthroned and by the painting Adoration of the Child with the Saints Secondiano and Jerome by Bernardino Fungai. Even in the more isolated places such as Montefollonico it is possible to discover hidden treasures: one of the most refined bas-reliefs in polychrome terracotta moulded by Francesco di Giorgio and one of his collaborators (ca.1490-95) and the Madonna and Child carved with softness of forms and polychromed with bright hues which stands out against a landscape painted in the background.
Further away close to the border with the Lazio region, in San Casciano dei Bagni, the collegiate church of San Leonardo preserves the altarpiece Coronation of the Virgin and Saints by Pietro di Francesco Orioli in which is represented the city offered by San Casciano to the Divinity. For nearby Sarteano two important artworks were created, attesting to the development of the Sienese art at the beginning of the sixteenth-century: The Annunciation by Girolamo del Pacchia in the church of San Lorenzo and the Annunciation by Beccafumi in the church of Santi Martino e Vittoria.