Montepulciano, Italy: A Guide to the Wine City!

Montepulciano in Italy is a popular tourist destination in Tuscany and a true paradise for connoisseurs and wine lovers. Beautifully situated on a hill in the Val d’Orcia, surrounded by green vineyards and olive groves, this medieval town offers an exceptionally charming scenery. Walking through the old town of Montepulciano, you will be amazed by the abundance of historic buildings, impressive churches and picturesque squares. Among the most stunning attractions in Montepulciano are the picturesque Piazza Grande and the Cathedral of Santa Maria Assunta. A real highlight is, of course, the Vino Nobile di Montepulciano, an exquisite red wine that is famous far beyond the borders of Italy and can be tasted locally.

In this travel guide we give you all the important information and tips about Montepulciano in Italy. We also show you amazing pictures, the best things to do and excursions, exclusive insider tips and where to stay in Montepulciano.

Good to know!

Around Montepulciano, you can find great agriturismo accommodations. An insider tip is Lupaia, a stunningly beautiful farmhouse with a pool and wonderful flair!

Montepulciano is a great starting point for exploring the beautiful Val d’Orcia. Towns like PienzaMontalcino and Monticchiello are just some of the highlights of the region!

Be sure to taste the excellent Vino Nobile di Montepulciano, a fine red wine that has been produced here since the Middle Ages and has made the town so famous.

Guided tours of Montepulciano and the surrounding area, as well as cooking classes, cheese and wine tastings, are also available online at GetyourGuide.

General Information about Montepulciano

Montepulciano is a small town in Italy with about 14,000 inhabitants and is one of the most beautiful attractions in Tuscany, thanks to the charming old town and the enchanting landscape. It is located on a hill about 600 meters high, in the famous Val d’Orcia, about 50 kilometers from the city of Siena and 90 kilometers from Florence. The heart of the town is the historical center, surrounded by a medieval wall, where you can visit numerous attractions during a tour. Nearby is the DOCG wine region of Montepulciano, where the world-famous Vino Nobile di Montepulciano is produced from the Prugnolo Gentile grape.

The history of Montepulciano dates back to the Etruscan era, and the town was first mentioned in 715 BC. Later, the town was alternately under the protection of Siena and Florence, remaining definitively Florentine at the beginning of the 16th century, becoming a bishop’s see in 1561. One of the most important events in Montepulciano is the Bravìo delle Botti, which takes place every year on the last Sunday in August. In this competition, wine barrels weighing about 80 kg are rolled up the alley to the main square to compete for a painted cloth, just like in the Middle Ages.


Things to Do in Montepulciano

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

Cathedral of Santa Maria Assunta

One of the most beautiful attractions of Montepulciano is the Cathedral of Santa Maria Assunta. It is located in the famous Piazza Grande, at the upper end of the town. For almost 100 years, from 1586 to 1680, it was built according to the design of Ippolito Scalza, although the façade has never been completed. The imposing bell tower on the left 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

The Piazza Grande is the most beautiful square in Montepulciano and has always been the center of civic and social life. There are a number of interesting attractions and fascinating monumental buildings. The Duomo, the Town Hall with its clock tower, Palazzo Contucci and, not to be forgotten, the Pozzo dei Grifi e dei Leoni, a true jewel of the historic center. Also unique are the cozy cafés at the Piazza Grande, where you can take a break from sightseeing and watch the hustle and bustle.

Tip: The apartment Contucci Residenze d’Epoca is an insider tip! It is located in a 500-year-old palazzo overlooking the Piazza Grande.

Town Hall Palazzo Comunale

A truly popular attraction in Montepulciano is the Palazzo Comunale, the town hall of the city. This stunning 14th-century palace has an enchanting façade and an imposing fortified tower reminiscent of the Palazzo Vecchio in Florence. Climbing the tower is also highly recommended. From the top, you can enjoy a wonderful view over the old town and the picturesque surroundings of Montepulciano!

The Well of the Griffins and Lions

The Well of the Griffins and Lions, also known as Il Pozzo dei Grifi e dei Leoni, dates back to 1520 and is located at 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 the Piazza Grande. Of interest are the two Etruscan columns and the fountain beam with the two lions with the Medici coat of arms.

Tip: Next to the fountain is the Bar Gelateria Duomo, where you can enjoy a coffee, some ice cream or a glass of wine in a breathtaking setting.

The Alleys of the Old Town

Montepulciano and its charming alleys are best explored by walking around the town on your own. Especially impressive are the historic townhouses and palaces that line the medieval streets. However, Montepulciano is also known for the many good delicatessen stores where you can taste and buy fine wines, cheese and specialties made of wild boar. For a coffee break, we recommend the Caffè Poliziano, a wonderful historic 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 Cantina Contucci is very interesting and a real insider tip, especially for wine lovers. It is located in a 16th century palace and has a wine cellar that can be visited free of charge. During a tour, you will be amazed by the huge barrels in which the famous Vino Nobile di Montepulciano is aged. Afterward, there is a free wine tasting and, if you wish, a shop where you can buy this excellent wine as a souvenir for friends and family.

Torre di Pulcinella

The Torre di Pulcinella, a small clock tower in the marvelous Piazza Michelozzo, is a real gem and a popular photo opportunity in Montepulciano. Of particular interest is the figure of Pulcinella, a symbol of Naples, which stands at the top of the tower and strikes the hour. Why this figure, rather untypical for Tuscany, beats the drum is still uncertain. Nevertheless, it is a beautiful place in the heart of Montepulciano and should not be missed on any tour of the town.

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, that is even said to have miraculous powers.

Things to do around Montepulciano

It is not only the town of Montepulciano that is worth a visit, but also the surrounding area that you will fall in love with. 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.

In the area around Montepulciano you can visit several charming towns such as Pienza, Monticchiello, Montalcino and San Quirico d’Orcia.

But also a trip to Bagno Vignoni with its wonderful healing springs and an excursion to Bagni San Filippo is highly recommended!

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


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 nice pool. This is the accommodation for a special vacation in Montepulciano!
  • Vacation Apartment in the Center: The Contucci Residenze d’Epoca is an insider tip! It is located in a 500-year-old palazzo with a wine cellar in Piazza Grande.

Find the best accommodation in Montepulciano:

More places to visit in Tuscany:

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