One of the twelve cities of the Etruscan League-substantial fragments of its primitive cyclopean defences can still be seen, incorporated in the medieval walls. Apart from a few fine Renaissance palaces, the prevailing character of Cortona's architecture is medieval, conferring on the steep narrow streets a strong sense of atmosphere. The city is commandingly situated (altitude 600 metres) and there are magnificent panoramas to every point of the compass, embracing the whole of the Val di Chiana.
This is the largest Comune in the Sienese Valdichiana and contains six other villages: Abbadia di Montepulciano, Acquaviva, Gracciano, Montepulciano Stazione, S.Albino and Valiano. The poet Agnolo Ambrogini (known as "il Poliziano" from the Latin "mons Politianus") was born here. The town is said to have been founded by the Etruscan king Porsenna and exhibits impressive architecture, mainly but not only Renaissance. Michelozzo, Baldassarre Peruzzi and Vignola all worked here, as did Antonio da Sangallo il Vecchio who designed the temple of San Biagio. Apart from the wonders of the historical centre of Montepulciano the tourist would do well to visit the spa centre at S.Albino. The local economy is based on agriculture and the town is famous for its Vino Nobile. In th summer the town hosts the "Cantiere Internazionale d'arte" and in the mid-Augut holidays the "Bruscello", a traditional show spoken in rhyme, is performed on the Cathedral steps. On August 29 a wine barrel race, the "Bravìo", is run between the different contrade, or districts, of the town and there is a procession in 13th-century dress.
The town stands on the top of a hill which overlooks the splendid Val d'Orcia. Enea Silvio Piccolomini was born here in 1405 and when he became pope Pius II in 1458 he decided to transform his modest village into the perfect town, an admirable example of the humanistic period, and entrusted the design to Bernardo Rossellino.
Piazza Pio II is intact, incorporanting the most rigorous of Renaissance perspective, and containing the cathedral and Palazzo Piccolomini.
The town's main axis is corso Rossellino, lined with houses built by the nobility in the 14th century. Pienza is a mainly agricultural centre, particularly famous for its pecorino cheese. The traditional cheese show, "fiera del cacio" takes place on the first Sunday in September. The flower show "Pienza e i fiori" takes place in mid May. Also to be visited is Monticchiello, made famous by its "Teatro povero", a new play anacted each summer by the local inhabitants.
Etruscan times the Castiglione area, ruled by Chiusi, was primarily dedicated to the production of wheat. Around the 7th century A.D. the promontory proved to be a formidable defensive outpost for the Byzantine Duchy of Perugia against the neighbouring Longobard territory of Tuscany. Later Arezzo, Cortona and Perugia fought for the possession of Castiglione, which was finally subjected by Perugia. In the 1617 Castiglione became a duchy until 1648, when the area was taken over by the Apostolic Chamber of the Papal States. Rocca del Leone. This fortress, probably designed by Frate Elia Coppi, was built in 1247. The Pentagonal walls are sectioned off by four square and one triangular towers. Palazzo della Corgna. The 16th-century architect Jacopo Barozzi, called "Il Vignola", built this structure incorporanting the ancient houses of the formerly-powerful Baglioni family and the existing defensive walls.
The covered battlements that connect the Palace to the Fortress add to the typically feudal atmosphere of the place. The Niccolò Circignani, called "il Pomarancio", began painting in 1574 in the "Hall of the Feats of Ascanio della Corgna" and continued in the "Hall of the Feats of Ascanio della Corgna" and continued in the "Hall of the Judgements of Paris" and in the "Hall of the Fall of Phaeton". He and Giovanni Antonio Pandolfi painted the "Room of the Aeneid". The bizarre decoration of the "Room of the Metamorphoses" are particularly interesting.