7 Best Things to Do in Montepulciano, Italy

Montepulciano may not be as well known as the neighboring Tuscan cities of Florence and Siena, but it is definitely worth a visit. This small medieval town, perched high on a hilltop, is filled with impressive Renaissance architecture, family-run shops and restaurants, and some of Italy’s best red wines. In fact, wine lovers should move Montepulciano to the top of their Tuscany lists and take the time to explore the underground cellars and sample the region’s highly rated varietals.

Here’s how to spend a day in Montepulciano.

The Piazza Grande in Montepulciano.

Piazza Grande

Photo: Matej Kotula / Shutterstock.com

1. Piazza Grande

At the highest point of Montepulciano, Piazza Grande is the ideal place to start exploring. For centuries, this square has served as the main gathering point for the city’s citizens. If you are a fan of Twilight movie series, this place might look familiar — it appeared New Moon.

Take a seat in one of the local cafes and soak up the atmosphere of this ancient square or take some time to explore the buildings and shops that surround the square. Looming large is the Palazzo Comunale, or town hall, which bears a striking resemblance to the Palazzo Vecchio in Florence. Built in the 14th century, this is an ideal spot to get up high for views of the city and the surrounding Tuscan countryside.

The church of Madonna di San Biagio.

The church of Madonna di San Biagio.

Photo: Martin M303 / Shutterstock.com

2. Three Classical Italian Churches

Montepulciano Cathedral

In Piazza Grande is the Montepulciano Cathedral, often called Montepulciano Duomo. Designed by Ippolito Scalza, the cathedral was built between 1586 and 1680 and finally consecrated in 1712. The way the cathedral looks today is quite different from the original design and parts remain unfinished, including the facade. The result is a church that looks quite austere compared to its counterparts in nearby cities. But visitors will appreciate some of the important works of art inside, including Taddeo di Bartolo Assumption of Mary and Sano di Pietro’s Madonna del Pilastro.

Church of Sant’Agostino

The oldest church in town, the Church of Sant’Agostino, was founded in 1285 and restored in the 15th century. Some additional modifications have been made over the years. Like the cathedral, Sant’Agostino is home to several important works of art, including a Virgin and Child fresco by Ambrogio Lorenzetti and Temptation of Saint Anthony by Rutilio Manetti.

Church of Madonna Di San Biagio

The Church of the Madonna di San Biagio, also known as the Church of San Biagio, is easily recognized by its large dome. Built between 1518 and 1540, this church is considered a masterpiece of Italian Renaissance architecture. Since it is below the town, it is best visited on your way to or from Montepulciano.

3. Learn about the history of Montepulciano

The Museo Civico di Montepulciano is housed in the 14th-century Palazzo Neri Orselli. The collection includes paintings and objects from the Etruscans (eighth century BC) to the 19th century. Among the museum’s most popular exhibits are Caravaggio’s Portrait of a nobleman and the terracotta of Luca della Robbia. Since most of the signage here is in Italian, an audio guide is recommended for English speakers.

Shops and restaurants in Montepulciano.

Shops and restaurants Montepulciano

Photo: InnaFelker / Shutterstock.com

4. Take a stroll down Il Corso

To see more of Montepulciano, take a stroll down its main street, Il Corso, which is also known as Via di Gracciano, Via di Voltaia, Via dell’Opio and Via Poliziano. Along the way, admire the many beautiful buildings such as Palazzo Avignonesi, Palazzo di Bucelli and Palazzo Cocconi. These were once the homes of the city’s wealthiest and most powerful citizens. None are open to the public, but all can be admired from the outside.

Il Corso is also home to a variety of cafes, bars, restaurants and shops. Be sure to browse all the offerings along this charming street.

Hopefully you’ve brought an extra bag for all the goodies you’ll be bringing home from Montepulciano. Or better yet, arrange for larger and heavier items to be shipped home — many stores here are happy to arrange this for you.

Like other towns in Tuscany, Montepulciano offers high-quality leather goods, but often at better prices. For handmade diaries, journals and photo albums, check out Legatoria Koine. For shoes, bags, coats and belts, head to Maledetti Toscani, which has been in business since 1848.

For high-quality linens such as bed linen, towels and tablecloths, visit Eredi Biagianti. This store also sells fabrics that can be used for custom orders.

Montepulciano is also known for its products made from olive wood, such as cutting boards, bowls and serving utensils. La Favola di Orfeo is the ideal place to shop for these items, as well as ceramics.

A wine cellar in Montepulciano, Italy.

Montepulciano winery

Photo: Simona Bottone / Shutterstock.com

6. Montepulciano wine

If you are a red wine lover, then Montepulciano is definitely for you. In fact, wine lovers may want to skip the sights and just enjoy the wide range of tasting opportunities here.

This area is known for Vino Nobile di Montepulciano, which has long been the preferred wine of kings, nobles and religious leaders in Italy. By law, this wine can only be produced in Montepulciano, must contain at least 70 percent Sangiovese and is aged for at least two years. While this wine can be enjoyed immediately after purchase, it also ages well.

You don’t have to leave the town of Montepulciano for wine tasting. Beneath the city streets are many cellars, making it easy for wineries to offer accessible tasting rooms. Consider starting at the Contucci winery, which is over 1,000 years old. Afterwards, continue to one of the area’s most popular wineries, Cantina De’Ricci. If you get hungry, the Ercolani Winery offers a wide variety of food in addition to delicious wines.

If you have more time, head out of town to visit some of the surrounding vineyards. Poliziano is one of the largest wineries in the area and offers guided tours including the vineyard, cellar, archives and wine tasting. Avignonesi is another well-known winery outside of Montepulciano that offers tours, tastings and some unique experiences like a hot air balloon ride over the Tuscan countryside.

If you want to visit some wineries without the hassle of driving, consider booking a tour. Excursions may also include additional sightseeing, lunch and the opportunity to sample local foods.

7. Montepulciano restaurants

As with all of Tuscany, there is a long list of food specialties to try in Montepulciano. Florentine excellentor pork with rosemary, fennel and sage, is a well-known dish. Pici pasta, believed to have been invented in Siena, can also be found in restaurants here. This thick water and flour spaghetti is often served with tomato sauce and topped with grated pecorino. The area is also known for its excellent olive oil and honey.

Caffee Poliziano

If you’re looking for a light snack or coffee, head to the historic Caffe Poliziano. Not only is the food good, but the view over the countryside is outstanding.

Enoteca La Dolce Vita

For fine meat and cheese dishes to accompany a good bottle of Vino Nobile, check out Enoteca La Dolce Vita.

Osteria Acquacheta

For great Tuscan steak, make a reservation at Osteria Acquacheta. This is one of the best-rated restaurants in town, but it fills up quickly, so be sure to make a reservation.

Cooking lessons

Instead of having your food served to you, consider taking a cooking class to learn the secrets of Tuscan cuisine. The cooking class at Le Caggiole lasts 5 hours and includes an appetizer, two types of pasta and a dessert. Another popular option is the pasta making class offered by Cesarine.

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