The town is situated at the top of the hill commanding the Valdichiana and the Val d’Orcia. It is renowned for its excellent wines, chief among which is the Vino Nobile. The rich fabric of the town is made even more fascinating by the intricate network of steep, narrow, twisting alleyways flanked on either side by buildings of prevalently Renaissance flavor.
An ancient Etruscan settlement said to have been founded by Lars Porsenna, it was mentioned in a document dated 715 as Mons Politianus. In the 13th century it was conquered by Siena, becoming a Florentine dominion toward the middle of the 14th century. Angelo Ambrogini, known as Poliziano, the elegant, cultured poet of the Medici court, was born here. So was Cardinal Roberto Bellarmino, the zealous supporter of the Counter-Reformation, instrumental in encouraging the development of Baroque Art.
Along the main street Via ROma flanked by 16th-century buildings, we find Palazzo Avignonesi, a late Renaissance building attributed to Vignola, with two superimposed orders of elegant windows. Further on is the 15th-century church of Sant’Agostino by Michelozzo, who also made the find terracotta relief above the portal, in which the Gothic influence is still apparent. The aisleless interior restructured in the 18th century, contains a San Bernardino da Siena by Giovanni di Paolo. Via Roma continues as Via Cavour to Palazzo Cervini, with rusticated stone facing designed by Antonio da Sangallo the elder.
In Via Garibaldi is the house of Poliziano from the period across the 14th and 15th centuries, restructured and number of times. The center of town is Piazza Grande, at the top of the hill surrounded by fine buildings such as the communal Palace from the 14th century with the façade attributed to Michelozzo and a handsome inner courtyard from the 14th century; austere palazzo Contucci by Antonio da Sangallo the elder; Palazzo Tartugi, attributed either to Vignola or Antonio da Sangallo the Elder, with a double loggia, on the ground floor and on the upper story; the Cathedral, a late 16th-century work by Scalza, which contains sculptures by Michelozzo, parts of a sepulcher dismantled in the 17th century, lost and rediscovered in the 19th century, together with a fine triptych of the assumption by Taddeo di Bartolo.
Not far off is the civic museum with works of the Florentine and Sienese schools from the 13th through the 18th centuries. Just outside the town is the church of San Biagio, or Saint Blaise, a masterpiece by Antonio da Sangallo the Elder completed in 1545 and a luminous example of Tuscan Renaissance architecture. The nearby Canonic, or rectory, is from 1595 designed by Sangallo is an extraordinary harmonious construction.
From here you can continue on through Val di Chiana, reaching the delicious Chianciano Terme and then Chiusi.