For the 50+ Traveler

Montepulciano may not be as well known as the neighboring Tuscan cities of Florence and Siena, but it is definitely worth visiting. This small medieval town, perched high on a hilltop, is full of impressive Renaissance architecture, family-owned shops and restaurants, and some of Italy’s best red wines. In fact, wine lovers should move Montepulciano to the top of their Tuscany bucket lists and make 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.

Explore The Piazza Grande

Located at the highest point in Montepulciano, the Piazza Grande is an ideal spot to start your exploration. For centuries, this plaza has served as the primary gathering spot for the town’s citizens. If you’re a fan of the Twilight movie series, this place may look familiar -- it was featured in New Moon.

Grab a seat at one of the local cafes and soak in the ambience of this ancient piazza, 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 the Madonna di San Biagio.

Admire Three Classic Italian Churches

Located on the Piazza Grande is the Montepulciano Cathedral, often called the Montepulciano Duomo. Designed by Ippolito Scalza, the cathedral was built between 1586 and 1680 and was finally consecrated in 1712. The way the cathedral looks today is quite different from the original design, and parts still remain incomplete, including the facade. The result is a church that appears 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’s Assumption of the Virgin and Sano di Pietro’s Madonna del Pilastro.

The oldest church in the city, the Church of Sant’Agostino, was founded in 1285 and restored in the 15th century. A number of additional modifications have taken place over the years. Like the cathedral, Sant’Agostino houses many important works of art, including a fresco of the Madonna and Child by Ambrogio Lorenzetti and the Temptation of Saint Anthony by Rutilio Manetti.

The Church of the Madonna di San Biagio, also known as the Temple 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’s located below the city, it’s best to visit it on your way into or out of Montepulciano.

Learn About Montepulciano’s History

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

Shops and restaurants in Montepulciano.

Stroll Down Il Corso

To see more of Montepulciano, stroll down its main street, Il Corso, which is also known as the Via di Gracciano, Via di Voltaia, Via dell’Opio, and Via Poliziano. Along the way, admire the many beautiful buildings, including the 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 outside.

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

Shopping In Montepulciano

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

Like other Tuscan towns, Montepulciano offers high-quality leather goods, but often for 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 like bedding, towels, and tablecloths, visit Eredi Biagianti. This shop also sells fabrics that can be used for custom orders.

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

A wine cellar in Montepulciano, Italy.

Appreciate The Wine

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

This region is known for Vino Nobile, which has long been the preferred wine of kings, nobility, 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 a minimum of two years. While this wine can be enjoyed right after purchasing, it also ages well.

You don’t need to leave the city of Montepulciano for wine tasting. Beneath the city streets are numerous cellars, making it easy for wineries to offer accessible tasting rooms. Consider starting at Contucci Winery, which is over 1,000 years old. Then continue on to one of the most popular wineries in the region, Cantina De’Ricci. If you get hungry, the Ercolani Winery offers a great selection 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 larger wineries in the region and offers tours that include the vineyard, cellar, archives, and wine tasting. Avignonesi is another well-known winery outside Montepulciano that offers tours, tastings, and some unique experiences like balloon rides over the Tuscan countryside.

If you want to visit a few wineries without the hassle of driving, then consider booking a tour. Tours may also include additional sights, lunch, and the chance to sample regional foods.

Eating In Montepulciano

As is true of all of Tuscany, there is a long list of food specialties to try in Montepulciano. Florentine arista, or 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 spaghetti made of water and flour is often served with a tomato sauce and topped with grated pecorino. The region is also known for excellent olive oil and honey.

If you’re looking for a light snack or coffee, head to the historic Caffe Poliziano. Not only is the food good, but the views of the countryside are excellent. For fine meat and cheese plates to accompany a good bottle of Vino Nobile, check out Enoteca La Dolce Vita. When you’re ready for a full meal, grab a table at Pane Vino & Zucchero. This family-owned restaurant sources much of its menu from its farm. For great Tuscan steak, make a reservation at Osteria Acquacheta. This is one of the top-rated restaurants in town, but it does fill up quickly, so be sure to make a reservation.

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 takes place over 5 hours and includes an appetizer, two types of pasta, and a dessert. Another popular option is the pasta-making class offered by Cesarine.