Montepulciano, is a medieval and renaissance hill town built along the narrow limestone ridge of Monte Poliziano 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 (Vino Nobile di Montepulicano e Rosso di Montepulciano).
The name of Montepulciano derives from Latin Mons and Publicianus ("Mount of Publicianus").  According to legend, it was founded by the Etruscan King Porsenna of Chiusi and recent findings prove that a settlement was already in existence in the 4th-3rd centuries BC.  In Roman times, it was the seat of a garrison guarding the main roads of the area.
After the fall of the Western Roman Empire, Montepulciano developed as a religious center under the Lombards.  In the 12th century, it was repeatedly attacked by the Republic of Siena.  The 14th century was characterized by constant struggles between the local noble families, until the Del Pecora family became rulers of the town.  From 1390 Montepulciano was a loyal ally (and later possession) of Florence and, until mid-16th century, lived a period of splendour with architects such as Antonio da Sangallo the Elder, Jacopo Barozzi da Vignola, Baldassarre Peruzzi, Ippolito Scalza, and others, building luxurious residences etc here.  In 1559, when Siena was conquered by Florence and Montepulciano lost its strategic role, its importance declined.
After the unification of Italy in the late 1800s and the drying of the Chiana Valley, the town remained the most important agricultural centre in the area, while most of the industrial activities moved towards Chiusi, where the railroad was being built.
There is plenty to visit in this beautiful, Tuscan hill town.  The long, winding main street, called the Corso, stretches for 1.5 kilometers from the Porta al Prato to the Piazza Grande at the top of the hill.  The following are worth a visit:

The Palazzo Comunale, designed by Michelozzo in the style of the Palazzo della Signoria (Palazzo Vecchio) of Florence.

Palazzo Tarugi, attributed to Antonio da Sangallo the Elder or Jacopo Barozzi da Vignola. It is entirely in travertine, with a portico which was once opened to the public.

The Cathedral of Santa Maria Assunta, or the Duomo of Montepulciano, constructed between 1594 and 1680 from plans by Scalza, includes a masterpiece from the Sienese School, a massive Assumption of the Virgin triptych painted by Taddeo di Bartolo in 1401.
The church of Santa Maria delle Grazie (late 16th century) has a simple Mannerist façade with a three-arcade portico.  The interior has a single nave, and houses a precious terracotta altar by Andrea della Robbia.

The Sanctuary of the Madonna di San Biagio, on the road to Chianciano outside the city, is a typical 16th century Tuscan edifice, designed by Antonio da Sangallo the Younger on a pre-existing Pieve, between 1518 and 1545.  It has a circular (central) plan with a large dome over a terrace and a squared tambour.  The exterior, with two bell towers, is built in white travertine.

Notable among the civic buildings are the Tarugi palace, like the Mercato, a work of Pignola, the Contucci palace designed by Sangallo and the fourteenth-century Palazzo Municipale, which contains a small gallery of Sienese and of Umbrian art.
The walls of the city were designed and built under the direction of Grand Duke Cosimo I de' Medici in 1511 by Antonio da Sangallo the Elder.

Montepulciano is also host to many cultural events.  In July-August there is Cantiere Internazionale d'Arte, an arts festival created by the German composer Hans Werner Henze.  In August there are two festivals: the Bruscello takes place on the 14th, 15th and 16th, when hordes of actors reenact scenes from the town's turbulent history;  and the Bravio delle Botti, on the last Sunday in August, sees a parade through the streets followed by a barrel race and a banquet.