Montepulciano - (45 Km)
Montepulciano, is built along a narrow limestone ridge and, at 605 m (1,950 ft) above sea level. The town is encircled by walls and fortifications designed by Antonio da Sangallo the Elder in 1511 for Cosimo I. Inside the walls the streets are crammed with Renaissance-style palazzi and churches, but the town is chiefly known for its good local Vino Nobile wines. a long, winding street called the Corso climbs up into the main square, which crowns the summit of the hill.
In August there are two festivals: the Bruscello takes place on the 14th, 15th and 16th, when hordes of actors re-enact scenes from the town's turbulent history. For the Bravio delle Botti, on the last Sunday in August, there is a parade through the streets followed by a barrel race and a banquet to end the day.
Madonna di San Biagio This beautiful church is on the outskirts of Montepulciano. Built of honey - and cream - colored travertine, it is Sangallo's masterpiece, a Renaissance gem begun in 1518. The project occupied him until his daeth in 1534.
Palazzo Bucelli The lower façade of the palazzo (1648) is studded with ancient Etruscan relieves and funerary urns collected by its 18th-century antiquarian owner, Pietro Bucelli.
Sant'Agostino Michelozzo built the church in 1427, with an elaborate carved portal featuring the Virgin and child flanked by St. John and St. Augustine.
Palazzo Comunale In the 15th century, Michelozzo added a tower and façade to the original Gothic town hall. The building is now a smaller version of the Palazzo Vecchio. On a clean day, the views that can be seen from the tower are superb.
Palazzo Tarugi The imposing 16th-century palazzo is next to the town hall and is currently undergoing restoration to the façade.
The Duomo was designed between 1592 and 1630 by Ippolito Scalza. The façade is unfinished and plain, but the interior is Classical in proportions. It is the setting for an earlier masterpiece from the Siena School, the "Assumption of the Virgin" triptych painted by Taddeo di Bartolo in 1401.
Pienza was rebuilt from a village called Corsignano, which was the birthplace (1405) of Aeneas Silvius Piccolomini (Italian: Enea Silvio Piccolomini), a Renaissance humanist born into an exiled Sienese family, who later became Pope Pius II. Once he became Pope, Piccolomini had the entire village rebuilt as an ideal Renaissance town. Intended as a retreat from Rome, it represents the first application of humanist urban planning concepts, creating an impetus for planning that was adopted in other Italian towns and cities and eventually spread to other European centers.
The rebuilding was done by Florentine architect Bernardo Gambarelli (known as Bernardo Rossellino) who may have worked with the humanist and architect Leon Battista Alberti, though there are no documents to prove it for sure. Alberti was in the employ of the Papal Curia at the time and served as an advisor to Pius. Construction started about 1459. Pope Pius II consecrated the Duomo on August 29, 1462, during his long summer visit. He included a detailed description of the structures in his Commentaries, written during the last two years of his life.