Montepulciano: A Guide to the Wine City!

Montepulciano in Italy is a very popular destination in Tuscany and a real paradise for connoisseurs and wine lovers. Beautifully situated on a hill of the Val d’Orcia and surrounded by green vineyards and olive groves, this medieval town delights with an exceptionally enchanting setting. Among the most beautiful attractions in Montepulciano is the historic old town with the picturesque Piazza Grande, the cathedral Santa Maria Assunta, the town hall and of course the red wine Vino Nobile di Montepulciano, which is famous far beyond Italy’s borders.

In this travel guide we give you all the important information and tips for a visit to Montepulciano in Italy. We also show you amazing pictures, the most beautiful things to do and where the best accommodations.

Good to know!

Montepulciano is a fantastic starting point to explore the beautiful Val d’Orcia. Lovely towns like Montalcino, Monticchiello and Pienza are only a few of the most beautiful places to visit in this region!

During your visit, you should definitely try the excellent Vino Nobile di Montepulciano, a noble red wine that has been produced here since the Middle Ages and to which the town owes its fame.

Around Montepulciano you can find the popular Agriturismo accommodations. A real insider tip is the Lupaia, a breathtakingly beautiful farmhouse with pool and lots of flair!

General information about Montepulciano

The small town of Montepulciano is situated on a hill, about 600 meters high, in the beautiful Val d’Orcia and is about 50 kilometers from the city Siena. In the area around the town is the DOCG wine region of Montepulciano, where the famous wine Vino Nobile di Montepulciano is produced from the grape Prugnolo Gentile.

The history of Montepulciano dates back to the Etruscan period and the village had first been mentioned in 715 B.C. Later, the town was alternately under the protection of Siena and Florence, remaining Florentine for good at the beginning of the 16th century and becoming a bishop’s see in 1561.

One of the most important events in Montepulciano is the Bravìo delle Botti, which is held annually on the last Sunday of August. In this competition, wine barrels weighing about 80 kg are rolled up the alleyway to the main square to compete for a painted cloth, like in the Middle Ages.


Things to do in Montepulciano

When you travel to Montepulciano, a whole variety of attractions and places to visit awaits you. The highlight is the medieval old town, which is especially fascinating with its beautiful Renaissance buildings and the countless beautiful alleys. Here is a summary of the best things to do in Montepulciano at a glance:

Cathedral Santa Maria Assunta

One of the most beautiful attractions of Montepulciano is the cathedral Santa Maria Assunta. It is located on the famous Piazza Grande, at the upper end of the city. For almost 100 years, from 1586 to 1680, it had been built according to the design of Ippolito Scalza, although the façade has never been finished until today. The imposing bell tower on the left side is even older than the church and dates back to the 15th century.

The magnificent interior of this cathedral is also worth seeing. Here you can admire valuable works of art, such as the baptismal font on the left, the tomb of Bartolomeo Aragazzi by Michelozzo and the three-part painting “Assumption of the Virgin Mary” by Taddeo di Bartolo.

Piazza Grande

Piazza Grande is the most beautiful square in Montepulciano and has always been the center of civil and social life. Here you can find a whole range of interesting attractions and monumental buildings. Among these were the Duomo, the Town Hall with its clock tower, Palazzo Contucci and not to forget the fountain Il Pozzo dei Grifi e dei Leoni, a real jewel of the old town. Also unique are the cozy cafés on Piazza Grande, which invite you to take a break of sightseeing.

Town Hall Palazzo Comunale

Another popular attraction in Montepulciano is Palazzo Comunale, the town hall of the city. This beautiful palace from the 14th century impresses especially with its charming outer facade and its imposing fortified tower, which resembles Palazzo Vecchio in Florence. Really recommendable is also to climb the tower. From the top you can enjoy a wonderful view over the old town and the picturesque surroundings!

Gryphon and lion fountains

The fountain of the griffins and lions, also known as Il Pozzo dei Grifi e dei Leoni, dates back to 1520 and is located on the edge of the main square. The fountain was designed by Antonio da Sangallo, an Italian architect and fortress builder. This beautiful medieval fountain is one of the most popular photo spots in the old town and is the heart of Piazza Grande. Interesting here are the two columns from the Etruscan period and the fountain beam, where the two lions with the coat of arms of the Medici can be seen.

Tip: Right next to the fountain is the bar Gelateria Duomo, where you can enjoy a coffee or a glass of wine in a breathtaking setting.

The Alleys of the Old Town

Montepulciano is best explored on your own via a city walk. Especially impressive are the historic townhouses and palaces, which are located along the medieval alleys. However, Montepulciano is also known for the many good delicatessen stores where you can taste and buy good wines, cheese and specialties made of wild boar. For a coffee break, we recommend the Caffè Poliziano, a beautiful historical coffee house with a fantastic panoramic view over the hilly landscape of Montepulciano!

Tip: One of the most beautiful viewpoints of Montepulciano can be found in a side street at the edge of the old town, just around the corner from the Montepulciano Gallery.

Cantina Contucci

A visit to the Cantina Contucci is very interesting and a real insider tip, especially for wine fans. It is located in a palace from the 16th century and has a wine cellar which can be visited free of charge. During a tour, you will be amazed by the huge wine barrels in which the famous Vino Nobile di Montepulciano is matured. Afterwards there is a free vine tasting, and, if you wish, there is a shop to buy this excellent wine as a souvenir for friends and family.

Torre di Pulcinella

Another jewel and popular photo motif of Montepulciano is Torre di Puclinella, a small clock tower in Piazza Michelozzo. Of particular interest is the figure of Pulcinella, a symbol from Naples, who stands at the top of the tower and strikes the hour.

Church of Madonna di San Biagio

One of the most beautiful attractions of Montepulciano is the church Madonna di San Biagio. Located just below the old town, it is one of the most impressive central buildings of the Tuscan Renaissance. It was built between 1518 and 1548 from travertine stone according to a design by Antonio da Sangallo il Vecchio. The interior is also worth a visit because of the impressive frescoes that can still be admired today. The highlight is the “Madonna on the Throne with the Child”, an interesting work of art, to which even miraculous powers are attributed.

Things to do around Montepulciano

Montepulciano is a fantastic starting point to explore the most beautiful parts of Tuscany. Thanks to the good position in the uniquely beautiful Val d’Orcia and the good tourist offer, it is worth spending several days.

Near Montepulciano you can visit many beautiful villages like Pienza, Monticchiello, Montalcino and San Quirico d’Orcia. An excursion to Bagno Vignoni with its medicinal springs is also recommended.

In addition, from Montepulciano you have the possibility to visit the world-famous old town of Siena on a day trip, which is about 50 kilometers away.


Where to stay in Montepulciano

In Montepulciano, both in the historical center and in the surroundings, there is a wide range of beautiful accommodations. From the well-kept wineries, agriturismo with pool to B&BS and apartments, everything is represented here. Here are our recommendations for the best accommodations in Montepulciano…It’s worth a look!

  • Palazzo in the Old Town: The Palazzo Carletti is located directly in the old town and enchants its guests with an extraordinary beautiful ambience.
  • Beautiful Pension: The CUGUSI BnB is a cute pension with a fantastic view of Montepulciano. Here the excellent breakfast and the beautiful rooms will delight you.
  • Agriturismo with Pool: The Lupaia is a beautiful farmhouse with a sensational restaurant and a breathtaking pool. This is the accommodation for a very special vacation in Montepulciano!

Find the best accommodation in Montepulciano:

More places to visit in Tuscany:

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