Best Things to Do in Montepulciano

Piazza grande -Montepulciano, Tuscany

Montepulciano is known for its breathtaking views, medieval charm, and, most notably, its globally acclaimed Nobile di Montepulciano wine. True to its name (‘Monte’ means ‘Mountain’), Montepulciano sits on a ridge over 600 meters above sea level. This Tuscan hilltop town offers a delightful experience, with the best of Tuscany waiting to be savored. Discovering the highlights of Montepulciano involves more than traditional sightseeing, as the focus is on enjoying the serene ambiance, accompanied by a glass of wine overlooking the picturesque Tuscan landscape.

We have made this guide to show you the top attractions and the best things to do in this beautiful town.

How to get to Montepulciano

Plane to Montepulciano

Perugia and Florence both have airports and are about an hour and a half drive to the small town in Southern Tuscany.  

Train to Montepulciano

Montepulciano is not directly accessible by train, but you can take a train to nearby Chiusi-Chianciano Terme or Montepulciano-Stazione stations. From there, you can catch a local bus or hire a taxi to reach Montepulciano. The train journey itself offers stunning views of the Tuscan landscape.

Bus to Montepulciano

There are regular bus services connecting Montepulciano with major cities in Tuscany, including Florence and Siena. The bus station in Montepulciano is conveniently located near the town center, making it a convenient option for travellers.

Car to Montepulciano

If you prefer the flexibility of driving, renting a car is a great option. Montepulciano is well-connected by the A1 highway, which runs from Milan to Naples. The town is approximately 200 kilometres (124 miles) from Florence and around 120 kilometres (75 miles) from Rome. The journey is scenic, offering beautiful views of the Tuscan countryside.

Rent a car Tuscany

RENT A CAR Tuscany

The best way to experience Tuscany is to rent your own car! We recommend booking well in advance using price comparison sites like rental cars if traveling in the peak summer season.

What to do in Montepulciano

Quick Facts about Montepulciano

  • Montepulciano is one of the larger hill towns in Tuscany
  • It dates back to the 4th century BC, to the time when the land was inhabited by the Etruscans
  • The present-day Montepulciano took shape during the 14th century AD
  • Montepulciano has been featured in several films, such as The Twilight Saga: New Moon
  • The town is famous for its wine, specifically the famous Vino Nobile di Montepulciano
  • Wine is so important in Montepulciano that the town hosts every year a barrel rolling competition (Bravio delle Botti) between the 8 town district

Explore the Piazza Grande

Piazza grande -Montepulciano, Tuscany

Situated at the highest point in Montepulciano, Piazza Grande serves as an excellent starting point for your exploration. It stands as the main square, adorned with significant structures including the Town Hall, the Cathedral of the Assumption, Contucci Palace, Palazzo dei Capitani del Popolo, as well as the Well of the Grifi and the Lions.

While the Cathedral of Saint Mary of the Assumption in Montepulciano may not be the most intricately adorned church in Italy, it remains a noteworthy attraction worth visiting. 

Opening Hours And Ticket Price

The cathedral is open daily from 9:00 AM to 12:30 PM and 3:15 PM to 7:00 PM.
It is free to enter.

Palazzo Comunale

Palazzo Comunale​ -Montepulciano, Tuscany

In Montepulciano, where breathtaking views of the Tuscan countryside abound, the Palazzo Comunale stands out as the ultimate vantage point. For the most elevated and dramatic perspectives, ascend to the pinnacle of this historic structure.

While the views of the town below are undeniably stunning, it is the 360-degree panorama of the surrounding countryside that truly captivates and steals the spotlight.

Civic museum

This stands as Montepulciano’s foremost art gallery, situated within a remarkable 14th-century palazzo that is a rare example of Sienese architecture in the town. Serene, delightful, and away from the hustle, it provides an excellent refuge to appreciate exquisite art.

Within its walls, a diverse collection of artifacts unfolds, offering a journey through the history of Montepulciano, reaching back to the Etruscan and Roman eras. The gallery showcases remarkable sculptures and paintings spanning several centuries. Among its prized possessions is a 19th-century Caravaggio masterpiece titled “Portrait of a Gentleman.”

Explore a wine cellar

Best things to do in Montepulciano, Tuscany

Montepulciano is well known for its wine. Immerse yourself in the town’s wine culture by visiting various cellars like Avignonesi, Poliziano, and Boscarelli. These wine cellars offer guided tours, wine tastings, and insights into the winemaking process, often housed in historic buildings that contribute to a unique ambiance for wine enthusiasts.

No elaborate planning or transportation is necessary, as the wine bars are conveniently situated in the town center. It’s advisable to check each winery’s operating hours, considering some may close for lunch. Montepulciano is globally recognized for its fruitier Rosso di Montepulciano and the rich, deep red Vino Nobile di Montepulciano. The Tuscan region’s standout wine, Vino Nobile, sometimes dubbed the “king of the reds,” enjoys widespread popularity in Italy and is crafted from the Sangiovese grape.

Medici Fortress

Medici Fortress​​​ -Montepulciano, Tuscany

Located at the southern end of Montepulciano, the Medici Fortress may not offer walls to traverse or towers to ascend, but it presents the opportunity to wander through a botanical garden and indulge in wine tasting.

Within the fortress lies the Enoliteca Consorzio Vino Nobile, where you can sample a variety of wines, including Vino Nobile di Montepulciano, Rosso di Montepulciano, and Vin Santo di Montepulciano. While navigating through the shop, you’ll find yourself treading on glass floors, allowing you to gaze down into the excavations of the fortress below.

Sant’Agostino church

Sant’Agostino church ​​​​- Montepulciano, Tuscany

Not far from the main gate, you’ll come across the enchanting Sant’Agostino Church. Constructed from the same cream-colored stone as the rest of the city, the church, designed by Michelozzo, captivates with its beauty and uniqueness. Inside, a crucifix attributed to Donatello adds to its allure. Adjacent to the church, a tower rises, crowned by one of Montepulciano’s distinctive sights: a statue of Pulcinella!

Pulcinella, a character from the traditional commedia dell’arte, hails from Naples, making its presence here quite unexpected. According to local lore, a bishop of Neapolitan origins brought the statue, and it now stands proudly atop the tower, serving as a unique timekeeper for the city with a prominent position on the clock.

Church of the Madonna di San Biagio

Distinguished by its expansive dome, the Church of the Madonna di San Biagio, also referred to as the Temple of San Biagio, stands out as an iconic structure. Erected between 1518 and 1540, this church is hailed as a masterpiece of Italian Renaissance architecture. A quick 5-minute walk downhill from the city walls will lead you directly to this remarkable site. Those approaching from the main entrance will traverse a line of majestic cypress trees, guiding them to the impressive church.

Stroll the city streets

Best things to do in Montepulciano, Tuscany

Embark on a self-guided tour of Montepulciano by strolling along a lengthy, meandering street adorned with landmarks. This thoroughfare, seemingly changing names as it intersects smaller streets, provides a glimpse into the town’s charm. Montepulciano, characterized by its long and narrow layout, welcomes visitors at its north end through Porta al Prato. From here, a labyrinth of streets unfolds southward, culminating near Fortezza Medicea.

Upon entering the town via Porta al Prato, an uphill journey awaits until you reach the picturesque Piazza Grande. Known as Il Corso, the town’s main road undergoes several name changes, transforming into Via di Gracciano, Via di Voltaia, Via dell’Opio, and Via del Poliziano before concluding at Chiesa di Santa Maria dei Servi.

Venturing into the side streets from Il Corso unveils viewpoints, shops, wine cellars, and eateries. A highly recommended activity in Montepulciano is to amble along Il Corso and explore these intriguing side streets. The experience promises unexpected discoveries, ranging from quaint restaurants and boutique shops to tranquil corners away from the bustling tourist areas.

Go on a hike

Best things to do in Montepulciano, Tuscany

In addition to the myriad attractions within Montepulciano, be sure not to overlook the enticing hiking opportunities just beyond the town borders. Some of our most enjoyable days were spent traversing the scenic trails amidst the surrounding hills, many of which link to charming medieval towns.

A standout among these hikes is the 7km trail leading to the quaint village of Montefollonico. While the path resembles a broad dirt road, be prepared for some challenging ascents and descents. Another highly recommended hike is the route to Monticchiello from Montepulciano, a well-trodden path that takes less than two hours. This trail unfolds through picturesque landscapes of vineyards, olive groves, and farmland, offering a delightful rural experience. Don’t miss the chance to explore these trails and immerse yourself in the natural beauty connecting Montepulciano with its medieval neighbors.

Explore Val d’Orcia

Val d’orcia - Tuscany Italy

The Val d’Orcia is a captivating landscape adorned with rolling fields, bathed in golden light, and bordered by cypress trees that grace the winding paths leading to rustic villas. This picturesque panorama encapsulates the quintessential image of Tuscany and has earned the Val d’Orcia recognition as a UNESCO World Heritage Site, showcasing some of the region’s most breathtaking natural beauty. Driving through this enchanting valley often prompts frequent stops to marvel at the captivating scenery.

While Montepulciano itself is not situated within the Val d’Orcia, it sits just on its outskirts, serving as an ideal hub for venturing into the Val d’Orcia by car.

Thursday morning market

Every Thursday, there’s an authorized farmers market located behind the primary bus stop. The market, held on Thursday mornings, is a diverse blend of clothing, regional items, fruits, and fresh produce.

Yet, the standout attraction is undeniably the porchetta, a distinctive Italian stuffed pork roast particularly cherished in the heart of Tuscany. At the Montepulciano Thursday Market, various stalls offer this delectable treat. 

Attend a festival

Montepulciano hosts a variety of events throughout the year, and if your visit aligns with local festivals, you’re in for a treat.
If you have a keen interest in medieval customs, the Bravio delle Botti is a must-attend event. It stands as the most emblematic historical reenactment in Montepulciano. The eight Contrada partake in a barrel race, vying for the coveted painted cloth known as Bravìo. This challenging competition involves rolling 80 kg barrels along an uphill course. The Bravio, a tribute to Montepulciano’s patron saint, San Giovanni Decollato, unfailingly occurs on the last Sunday of August.
Cantine Aperte (Open Cellars) stands as Italy’s premier event for wine enthusiasts, and Montepulciano actively participates in this initiative, showcasing its centuries-old winemaking heritage. During the last weekend of May, visitors have the opportunity to explore historical wine cellars, take guided tours around the town, and unveil the most cherished treasure of Montepulciano: the grapes! On May 1st in Montepulciano, the Fair dedicated to Sant’Agnese takes place, featuring a historical procession through the town’s streets and a Mass at the Sant’Agnese shrine. This event commemorates the local Contrada, as Montepulciano is divided into 8 Contrade, resembling districts.
Held in February at the Medici Fortress on Via San Donato 21, Anteprima Vino Nobile is a gathering designed for both wine enthusiasts and industry professionals. This event offers a unique opportunity to sample an early taste of the latest Vino Nobile vintage, a flagship product of Montepulciano, along with other regional wines.


What to eat in Montepulcianno and where

Osteria Acquacheta is a beloved local eatery known for its hearty Tuscan fare and convivial atmosphere. Try their famous Bistecca alla Fiorentina, a Florentine-style T-bone steak, or their mouthwatering handmade pasta dishes. The rustic charm and flavourful dishes make it a must-visit.

Ristorante La Grotta offers an upscale dining experience in a historic setting. The menu features traditional Tuscan and Italian cuisine with a focus on locally sourced ingredients. Dishes like Pici pasta with truffles and grilled Chianina beef are highlights.

E Lucevan le Stelle is a charming restaurant with a menu that combines Italian and Mediterranean flavors. You can savor fresh seafood, homemade pasta, and a variety of delectable dishes. The warm and welcoming atmosphere makes it a great choice for a relaxing meal.

For excellent meat and cheese platters to complement a quality bottle of Vino Nobile, be sure to visit Enoteca La Dolce Vita.

Caffè Poliziano, named in honor of Agnolo Poliziano (1454-1494),  offers a café with pastries and take-out options on the main floor, while the lower floor features an indoor dining area and a breathtaking terrace.

Other notable restaurants are La Vineria di Montepulciano, La Taverna di San Giuseppe, Osteria di Casa Chianti and Panineria Al Vicolino.

Where to Stay in Montepulcianno

Il Rondò Boutique Hotel is a charming and luxurious boutique hotel situated within the historic center of Montepulciano. The hotel boasts elegant rooms, a beautiful garden, and a wine bar. It’s an ideal choice for those seeking a refined and romantic getaway.
Address: Via di Martiena, 9, 53045 Montepulciano SI

Palazzo Carletti is a historic residence that has been transformed into an inviting hotel. With its central location, comfortable rooms, and a charming courtyard, it offers a delightful stay for guests looking for a mix of history and comfort.
Address: Via dell’Opio nel Corso, 3, 53045 Montepulciano SI

La Terrazza Di Montepulciano is a family-run hotel known for its welcoming atmosphere and fantastic views. The rooms are cozy, and the terrace provides breathtaking vistas of the surrounding countryside. It’s an excellent choice for those who appreciate a personal touch.
Address: Via Pié al Sasso, 16, 53045 Montepulciano SI


How much time do you need in montepulciano?

Exploring the key attractions in Montepulciano typically requires approximately four hours or half a day. This timeframe allows for leisurely strolls through the city, shopping, ascending the clock tower, engaging in wine tastings at one or two locations, and enjoying a meal. For a more comprehensive experience, dedicating a full day enables thorough exploration of Montepulciano, including visits to multiple wine cellars for tastings.

Is Montepulciano worth visiting?

Known for its underground wine cellars and charming enotecas, this town stands out as the premier location to savor a diverse range of Vino Nobile di Montepulciano. Even if wine tasting isn’t your primary focus, Montepulciano offers a delightful exploration experience, with its winding streets, panoramic views of Tuscany, and an array of boutique shops. So yes Montepulciano is absolutely worth visiting!

When is the best time to visit Montepulciano?

The optimal period to explore Montepulciano is in late spring, from May to mid-June, when the Val d’Orcia fields exhibit a lush, vibrant green. Another favorable time is from September to October, coinciding with the harvest season and a pleasant cooling of temperatures. The summer months, characterized by significant crowds and high temperatures, are less ideal.

Are there any tips for visiting Montepulciano?

Exploring Montepulciano is most enjoyable on foot, given its small walled layout. Convenient parking is accessible just outside the city walls, operating on a pay-and-display system. Both open-air and covered parking options are provided. Certain hotels may assist in obtaining permits for driving within the walled area, but we would advise caution when considering this option.  Opting for a car is the recommended mode of transportation to reach Montepulciano.

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