Val di Chiana

Visit Montepulciano in Val di Chiana
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Montepulciano, one of the most beautiful hamlets in Tuscany

Site of an ancient Etruscan castle, Montepulciano is located between the Val d’Orcia and the Val di Chiana; a border location long contended by Siena and Florence.

A castle and a parish (church of Santa Maria) are mentioned in 714 in some documents. These buildings were placed where now stands the Duomo (cathedral). In the 12th century, the importance of Montepulciano grew and with it grew even the urban fabric of the village that developed following the shape of the hillock on which it is located. At that time the town was provided with a new city walls. In 1232, the hamlet was conquered by Siena that razed its fortress, walls and towers.

These facilities were rebuilt, and expanded, in the second half of the 13th century. For nearly three centuries Montepulciano passed alternately under the control of Siena and Florence, while inside a merchant class was acquiring power. The development of trade was accompanied by a further growth of the urban plan.

In the early 15th century, Montepulciano came under the dominion of Florence. At that time started a process of urban rewal which continued even during the period of the House Lorraine (18th-19th centuries). Initially were restored the piazza Grande and the Town Hall. In the 16th century the town was raised to the rank of a bishopric and, during the rule of the Lorraine, the Cathedral was completed and the Teatro Poliziano was built.

During the 19th century, the Val di Chiana was reclaimed and, in 1844, the railway line was opened in the valley. This event led to displacement toward the plain of production and commercial activities. Today the city as well as being a tourist destination is very famous for the production of the Vino Nobile di Montepulciano.

Montepulciano panoramic view

Things to do in Montepulciano

Chiesa di Sant’Agnese

We begin our itinerary in Montepulciano starting from the Church of Sant’Agnese which is located just outside the walls of the historic center. Erected together with its convent from 1306, the church was enlarged during the 14th century. The facade of the church was rebuilt in 1926 but still retains the original portal. Inside there are the remains of the saint and numerous works of art of great value.

Leaving the church at the back, we pass through the Giardino Poggiofanti (garden) and the Monumento ai caduti in guerra (monument to the war dead), to reach Porta a Prato (a city gate). The city gate, of medieval origin but renovated in XVI and in XX century, is historically the main access to the city.

Via di Gracciano nel Corso

Beyond the door, take via di Gracciano nel Corso the first section of the main artery of the country. A few meters away from the door meets the column of Marzocco (a symbol of Florence). There are many interesting buildings overlooking via di Gracciano; one of these is Palazzo Bucelli that has its particularity in the basement in where were walled up several Etruscan finds.

Montepulciano roofs view

Chiesa di Sant’Agostino

Continuing on the road, we arrive at the foot of a staircase on top of which is the Chiesa di San’Agostino. It is a single-nave church with a semicircular apse founded in 1285 and completely renovated in 1429. This church has a remarkable facade in travertine built between the 15th and 16th centuries.

Visit Montepulciano Sant'Agostino
Church of Sant’Agostino (Photo by Alessandro Antonelli / CC BY)

In front of the church we report the Clock tower known as Torre di Pulcinella because of the unusual statue on top of the Neapolitan mask.
Continuing to climb the hill we come in Piazza delle Erbe. From here we continue following via di voltaia del Corso, via dell’Opio nel Corso, via del Poliziano and via San Donato and finally we reach the top where we find the most important monuments of Montepulciano.

Fortezza Medicea

Documented since the 8th century, it has been destroyed and rebuilt several times. The current building is the result of “style” nineteenth-century restoration. Currently some of its spaces are used to host fairs and events such as the Mostra dell’artigianato (a craft exhibition) which takes place annually.

things to do in Montepulciano: visit the The fortress
The fortress (Photo by Valeri Rossano / CC BY)

Piazza Grande, the heart of Montepulciano

The Piazza Grande in Montepulciano is one of the most beautiful in all of Tuscany. Political and religious center of the city, is the seat of the most important buildings. Here we find the Duomo (Cathedral), the Palazzo Comunale (Town Hall), Palazzo del Capitano, Palazzo Nobili-Tarugi and Palazzo Contucci.


The Cathedral of Montepulciano was built between 1594 and 1680, where the Pieve di Santa Maria previously stood. The Church has a Latin cross plan divided into three naves; the facade has unfortunately remained unfinished but the best is inside. On the left of the church stands the massive bell tower built for the parish church of Santa Maria during the fifteenth century.

The cathedral of Santa Maria Assunta preserves a remarkable heritage of works of art. Among these, I will just mention the fabulous Triptych of the Assumption by Taddeo di Bartolo and the delightful Altar of the Lilies by Andrea Della Robbia, however there are many others that deserve attention.

things to do in Montepulciano: visit the Duomo
Duomo (Photo by Geobia / CC BY)

Palazzo Comunale

Located on the right of the Duomo, this imposing turreted palace was built in the 14th century and renovated during the 15th century. It is a three-storey building, partially covered with ashlar with crenellated crowning, whose facade has been attributed to the great Florentine architect Michelozzo.

From the top of its tower you have an extraordinary view of the whole village and the surrounding area, therefore I absolutely recommend you buy your ticket and climb to the top.

Information on timetables and ticket prices for both the tower and the terrace of the Town Hall on the website of the Pro Loco of Montepulciano.

Palazzo Comunale in Montepulciano
Palazzo Comunale in Montepulciano

The Museo Civico Pinacoteca Crociani

Located in via Ricci at Palazzo Neri-Orselli, the Civic Museum houses various pictorial works, many of which come from the Crociani collection, some Della Robbia pottery and an archaeological section with Etruscan grave goods and Roman finds.

For more information on opening hours and admission prices, I refer you to the official website of the Museum.

Chiesa di San Biagio

The church of San Biagio stands in a beautiful position a short distance from the town. Built in the 16th century on a project by Antonio Giamberti da Sangallo, this temple is a magnificent example of Tuscan Renaissance architecture. San Biagio has a Greek cross plan with a central dome. The project involved the construction of two bell towers that were to flank the main facade but in the end only one was completed while the other was only started.

things to do in Montepulciano: visit the church of San Biagio
Church of San Biagio (Photo by Adrian Michael / CC BY)

The thermal baths of Montepulciano

Another reason to visit Montepulciano are its spas. The spa of the city is located in via delle terme just 5 kilometers from the historic center. In addition to the classic relaxation of the spa, the waters of this area offer valuable help for the treatment of respiratory diseases (asthma, bronchitis etc.).

What to see around Montepulciano

Montepulciano is located in the Sienese Val di Chiana a few kilometers from several interesting hamlets to visit such as Cortona, Torrita di Siena, Sarteano and Chiusi.

How to get to Montepulciano

Public transport: unfortunately Montepulciano is not served directly by the railway; the closest stations are those of Chiusi (if you take the train from Florence or Rome), Torrita di Siena and Buonconvento (if you depart from Siena). From these locations you can take buses that provide daily connections.

By car: coming from the A1 highway you must take the Valdichiana-Bettolle exit if you are coming from the north, while from the south the exit is Chiusi-Chianciano Terme. Coming from Siena, you could take the SR2 to San Quirico d’Orcia and then the SP146 to your destination. It is not the fastest road, however, it allows you to pass through Buonconvento and then cross the Val d’Orcia… not bad!
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