This beautiful Renaissance hilltown, which still adheres to its medieval plan, is embedded in a picture-postcard landscape: every way you turn, you are confronted with the iconic image of the Tuscan countryside, where waves of hills and golden fields, dotted with cypresses, roll and roll together.
Thanks to its superb vineyards, the Montepulciano area is considered one of the finest winemaking regions in the world, which makes it without a doubt one of the most frequented and beloved tourist destinations in Tuscany.
The best way to discover the elegant historic center is to walk it. Enter by Porta al Prato, in the lower part of the town, and walk uphill until you reach the summit and Piazza Grande, which hosts a great many cultural events of international significance. You will meet Renaissance palazzo after Renaissance palazzo, a slew of artisan workshops and beautifully façaded churches that are even more astonishing and interesting inside.
Palazzo Comunale: city hall designed by Michelozzo recalling 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 open to the public.
Santa Maria Assunta Cathedral, or the Duomo of Montepulciano, constructed 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.
Santa Maria delle Grazie: late 16th-century) church with 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.
Madonna di San Biagio Sanctuary: church, located on the road to Chianciano outside the city, it is a typical 16th century Tuscan edifice, designed by Antonio da Sangallo the Elder 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.
This church is considered an architectural triumph, so much so that Michelangelo cribbed from it when he was sketching the first drafts of what would become St Peter's Basilica in Rome.
Santa Lucia: Baroque church with altarpiece by Luca Signorelli.
Museo Civico di Montepulciano: located in the Palazzo Neri Orselli, displaying a collection of archeologic items, paintings, and terracotta works by the Della Robbia family
The walls of the city are circa 14th century.
The only way to get around within the historic center is to walk along the steep pathways. Driving within the historical old town is not permitted without fines unless you are a local with a permit. Outside the historic old town, a car is recommended to drive around the countryside and outer town. Road biking is also possible, although be wary of cars on the narrow, curving, and rolling roads.
But in spite of its indisputable beauty, Montepulciano is known throughout the world for its Vino Nobile: one of Tuscany's most globally valued wines, this red is made from grapes grown in the vineyards that surround the town.
The Vino Nobile di Montepulciano has Denominazione di origine controllata e garantita status and is, with the Brunello di Montalcino and Chianti Classico, one of the principal red wines of Tuscany. The Rosso di Montepulciano and Vin Santo di Montepulciano have Denominazione di origine controllata status.
Its local wine is traditionally considered one of Italy's best red wines and was lauded by the poet Francesco Redi as "the king of all wines!"
Don't miss a visit to at least one of the monumental wineries. Many of these are so interesting as pieces of architecture in their own right that they draw aesthetes as well as wine lovers.
Most of the shops and restaurants are on the main street, which stretches from Porta Al Prato to Piazza Grande for 1.5 kilometres.
Every year in August, the eight districts of Montepulciano compete in the Bravìo delle Botti, a race through the town's oldest streets, spiced up with flag-wavers and historic dress. The theatrical show Bruscello Poliziano comes to town around the same time, while the International Art Workshop welcomes tourists and the curious with the finest musical and artistic exhibitions. The Vino Nobile di Montepulciano Previews take place in February: an unmissable date for all wine lovers.
A stroll through the beauty of Montepulciano has to finish with a dinner made from the finest local produce, such as the Cinta Senese sausage or pappardelle pasta in wild boar sauce: all washed down, of course, with a glass of Vino Nobile. If you love fresh pasta, sit down in front of a plate of pici all'aglione (a thick pasta in garlic sauce), a condiment typical of the Val di Chiana. And finally, don't miss the chance to see a Chianina steak grilled on the table.
According to legend, it was founded by the Etruscan King Lars Porsena of Clusium (modern Chiusi). Recent findings prove that a settlement was 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, it developed as a religious center under the Lombards. In the 12th century it was repeatedly attacked by the Republic of Siena, which the Poliziani faced with the help of the Perugia and Orvieto, and sometimes Florence˙, communes. 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 the 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 and other edifices here. In 1559, when Siena was conquered by Florence and Montepulciano lost its strategic role, its importance declined.
After the unification of Italy and the drying of the Val di Chiana, the town remained the most important agricultural centre in the area, while the industrial activities moved mostly next to Chiusi, which was nearer to the railroad being built in that period.