Hello travelers! This article is the final part of our 3-day itinerary in the Chianti Region, with the last stop in Montepulciano.
The town has ancient roots, likely dating back to the Etruscan period. It first gained prominence in the Middle Ages and later flourished during the Renaissance under the influence of the Medici family.
Montepulciano is famous for its scenic views over the Val d’Orcia Valley, beautiful Renaissance architecture, and one of Italy’s most esteemed wines: Vino Nobile di Montepulciano.
While exploring Montepulciano, don’t forget to check out our other itineraries in the Chianti Region by looking at the Day 1 and Day 2 articles.
Itinerary
We’ve been traveling across the Chianti region by car since it is the most convenient way to move around. Many destinations in the region, including Montepulciano, are not reachable by train. We entered the town from the northern part and parked our car for free near Porta al Prato. Porta al Prato is one of the main gates leading into the historic town of Montepulciano. The town is not large and is easy to explore on foot. From here, it is just a 17-minute walk to the historical center.
1. Torre di Pulcinella
On your way to the town center, you’ll definitely pass by the Torre di Pulcinella, one of the unique landmarks in Montepulciano. The Torre di Pulcinella is a clock tower featuring the figure of Pulcinella, a character from the traditional Italian commedia dell’arte. The presence of this figure on the tower is somewhat mysterious, as Pulcinella is more commonly associated with Southern Italy, particularly Naples.
No one knows why a Neapolitan symbol is found in Montepulciano. According to legend, the Torre di Pulcinella was the idea of a bishop or a priest from Campania region who, in the 17th century, brought the clock from Naples as a tribute to his homeland. Others believe that it is not Pulcinella but another Renaissance figure, the Mangia of Siena, who was mistakenly identified with the Neapolitan mask.
2. Piazza Grande
3. Cathedral of Montepulciano
Italian: Cattedrale di Santa Maria Assunta
Here in Piazza Grande, the Cathedral of Santa Maria Assunta, known as the Duomo, is located. The Cathedral built between 1586 and 1680 to a design by the architect Ippolito Scalza, was erected on the site of the ancient parish church of Santa Maria. The Cathedral hosts several important artifacts such as the Assumption of the Virgin triptych, painted by Taddeo di Bartolo in 1401, the so-called Altar of the Lilies, a work by Andrea della Robbia dating to around 1512, and a pipe organ built between 1837 and 1838 by Filippo II Tronci.
Opening Hours: from Monday to Friday 8.30 am to 12.30 pm, from 2.00 pm to 5.00 pm
Ticket Price: free
4. Town Hall
Italian: Palazzo Comunale
The Palazzo Comunale of Montepulciano, also known as the Town Hall, overlooks Piazza Grande. Built in the 13th century in the Gothic style, it underwent renovations by Michelozzo during the 15th century. The striking resemblance between the Palazzo Comunale of Montepulciano and the Palazzo della Signoria in Florence is noteworthy, as it was personally commissioned by Cosimo I dei Medici. The Town Hall’s tower is open to visitors, providing a splendid panorama of the surrounding Chianti valleys.
Opening Hours: daily from 10.00 am to 6.00 pm
Ticket Price: the terrace – 2.50 €, the tower – 5 €
5. Palazzo Contucci
Located just beside the Piazza Grande on Via Del Teatro, this Renaissance palace offers guided tours of its historical cellars, where you can taste the famous Vino Nobile di Montepulciano. At Palazzo Contucci, you can admire the frescoes painted by Andrea Pozzo, visit the palace’s 16th-century internal courtyard, and join a tour of the monumental cellars underneath the Palazzo, among the oldest and most impressive in Montepulciano. You can opt for a wine tasting of the region’s pride, Montepulciano Vino Nobile, which can, on request, be accompanied by typical local foods. It is recommended to contact the staff of Palazzo Contucci for bookings, and prices in advance.
Opening Hours: 10:00 am to 6:30 pm.
6. Lunch at Osteria Acquacheta
You can’t go wrong with legume and porcini mushroom soup and a steak! Buon Apetito! Just don’t forget to book a table in advance as the tavern might get busy!
Lunch hours: 12.30 pm to 3.30 pm. Closed on Tuesdays.
Price Range: 20€ – 30€ per person
7. San Biagio Church
Italian: Tempio di San Biagio
After a hearty lunch, we head to the beautiful San Biagio Church, which is a 15-minute walk from the historical center. This Renaissance church is an architectural masterpiece designed by Antonio da Sangallo the Elder. The church was built on the site of an ancient parish church of early Christian origin dedicated to Santa Maria around the year 1000. It is quite unique, constructed according to the Greek cross plan, with a central dome supported by a drum.
The interior is also impressive, with a serene ambiance that invites contemplation and admiration of its artistic details. One of the famous artifacts is the 14th-century fresco, considered miraculous, depicting the Madonna enthroned with Child, known as the Madonna of San Biagio.
Opening Hours: 10.00 am to 6.00 pm daily. On Sundays, it is open from 11.30 am.
Ticket Price: 3.50€
8. Museo Civico
Even though the day has already been intense, you can’t miss the Civic Museum of Montepulciano, also called Pinacoteca Crociani. The museum is housed inside the fourteenth-century Palazzo Neri Orselli, a rare example of a building in the city that still preserves memories of Sienese architecture from the fourteenth century. It hosts some of the most important works and artifacts of the region.
The Crociani Art Gallery represents the most important part of the museum, consisting of approximately 180 works dating between the 14th and 19th centuries. Among the major works on display are the “Crucifixion” by Filippino Lippi and the “Holy Family” by Antonio Bazzi, known as Sodoma. There is also a small room dedicated to a single painting: a portrait of a gentleman, created toward the beginning of the 17th century and recently attributed to Caravaggio.
Opening Hours: 10.00 am to 6.00 pm daily. Closed on Tuesdays.
Ticket Price: 6€ – standard, 4€ – reduced for young people under 18 years old and elderly people over 65 years old.
9. Aperitivo at La Vineria
Don’t forget to book your table in advance as the place is quite popular!
Opening Hours: 12.00 pm to 10.00 pm
Price Range: 30€ – 40€ per person
Transport and Moving Around
We’ve been traveling across the Chianti region by car since it is the most convenient way to move around. Many destinations in the region, including Montepulciano, are not reachable by train. The nearest train stations to Montepulciano are in Arezzo and Perugia.
Distance from other cities to Montepulciano by car:
- Florence – around 1 hour 20 minutes
- Arezzo – around 40 minutes
- Perugia – around 1 hour
Summary
Check our alternative guide to magnificent Florence while traveling in Tuscany!
Florence is often considered the most beautiful city in Italy, not to say the entire world. As the birthplace of the Renaissance movement, Firenze is full of monuments, churches, museums, and sights waiting to be explored. And, of course,