Montepulciano, a town and commune in the province of Siena in southern Tuscany, (Italy), is a medieval and renaissance hill town of exceptional beauty. Montepulciano sits on a high limestone ridge, with an elevation of 605 m (around 2000 ft).

Montepulciano is a major producer of food and drink. Wine connoisseurs consider its Vino Nobile among Italy's best. However, the Vino Nobile de Montepulciano should not be confused with the varietal wine (Montepulciano grape) of the same name. Montepulciano is also known for its pork, cheese, "pici" pasta (a thick, rough, chewy variant on spaghetti), lentils, and honey.

The main street of Montepulciano stretches for 11.5 kilometers from the Porta al Prato to the Piazza Grande at the top of the hill. The city is renowned for its walkable, car-free nature. The main landmarks include:

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

The Cathedral of Santa Maria Assunta, or the Duomo of Montepulciano, contstructed between 1594 and 1680, 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). It 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. It 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.

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.