Encircled by walls and fortifications designed and built starting 1511 AD by Antonio da Sangallo on the orders of the great Florentine, Cosmo I, Montepulciano cascades down a limestone ridge whose highest point is over 600 meters (1950 feet) above sea level.
The long and winding main street of Montepulciano extends from the Porta al Prato for 11.5 km to the Piazza Grande, and will take the traveler through the old medieval districts of one of the most pleasant and satisfying of all Tuscan cities.
The Piazza, fronted by most of the city's most notable buildings, including the Palazzo Comunale and the Duomo, perches at the utmost top of the hill, where Poliziani (the name the citizens give to themselves) mingle with visitors from nearby and far away.
The Duomo, with its plain, almost unfinished facade, was designed and built by Ippolito Scalza in 1630. The most important work of art in the interior is a triptych done in 1401 by Bartolo, the "Assumption of the Virgin".
The Palazzo Comunale, a seemingly smaller version of Palazzo Vecchio, was built originally in the Gothic style, but the tower and facade were added in the 15th Century by Michelozzo. Visitors are welcome to climb the tower where breathtaking views over the city and across the Tuscan countryside can be absorbed. Next to the town hall is the Palazzo Tarugi, built in the 16th century.
Close by is the Chiesa Sant'Agostino, built in 1427 with a mix of Gothic and Renaissance elements by the architect, Michelozzo. Note the elaborately carved portal. The Palazzo Bucelli (1648), also close by, has a lower facade into which are integrated Etruscan bas relief and funerary urns.
The Church of Jesus was built with a quasi circular plan by the Jesuit architect, Fra Andrea Pozzo. Pozzo also worked on various other buildings in Montepulciano including the Palazzo Contucci (see above).
Sangallo the Elder also built the Temple of Madonna di San Biaglio, flanked by two campanile (bell towers) outside the city gates. It is also a Renaissance building built with butter- colored Travertine marble. Sangallo started it in 1518, and remained pre-occupied with it until his death in 1534 and it is rightly recognized as his masterpiece. The design influence or inspired the architects of many of the palazzi in Montepulciano such as Palazzi Avignose, Cocconi, Cervini, Ganoni-Grugni, Contucci and Tarug (see above).
Also outside the walls and worth a peek are Chiesa Santa Chiara and Chiera Santa Maria, both done in the Baroque style.
Montepulciano is, of course, famous for its wines, particularly the Vino Nobile, a mellow red wine that evokes the scent of flowers and is shot through with a kind of iridescent orange color. There are many less agreeable things to do than sit in one of the city's many cafes or restaurants to imbibe a glass (or two!) or purchase a bottle (or two!) at a local shop, which you can consume later during a lazy Tuscan picnic.
Montepulciano is also the scene of a few enlivening annual festivals. Arrive in late July-early August for the Cantiere Internazionale d'Arte arts festival founded by the German composer Hans Werner Henze. Re-enactments of Montepulciano's turbulent history take place at the Brucello festival in mid August, and there is a parade, barrel race and banquet at the end of August, the Bravio dell Botti.