Best Things to Do in Montalcino

Best Things to Do in Montalcino

Montalcino, a charming little idyll perched atop a hill in the province of Siena, is an ideal destination for visitors seeking to experience some of Tuscany’s world-famous red wine. Imagine a charming village with picturesque cobblestone streets, breathtaking views of the surrounding valley, a captivating medieval fortress, and, of course, an outstanding wine culture.

Montalcino, one of the top places in Italy for wine aficionados, is the acclaimed birthplace of Brunello di Montalcino, a red wine noted for its characteristics and coffee undertones. Numerous local vineyards and wineries offer enough possibilities for visitors to try the renowned wine variety, which played a significant influence in shaping the city as it is today.

But Montalcino is not only popular among wine enthusiasts. From archery tournaments to world-class wineries, this fascinating Tuscany town offers an abundance of activities. Best Things to Do in Montalcino.

If you’re already captivated by Montalcino’s allure but would like to learn more about the city before you visit, we’ve compiled essential information to help you organize the most memorable vacation.

19 Best Things To Do In Montalcino

1. The Abbey of Sant’Antimo

This abbey, believed to have been named after Saint Anthimus, was constructed prior to the year 814. It is unclear exactly when it existed, although historical records indicate it existed then. Thereafter, a settlement developed around the abbey. It is now one of the oldest functioning abbeys in Italy and a must-see attraction. A short distance from the town of Montalcino, the monastery plays Gregorian chants – a remnant of a former visit by French monks – and visitors may tour the church at designated hours.

2. Admire Montalcino Rocca

Montalcino’s skyline is dominated by the village’s fortress, which is positioned atop the town’s hill. The stronghold was constructed in 1361 when Montalcino was ruled by Siena, and it remains a formidable sight.

Tall walls and turrets are still standing and generally retain their original aspect. During our previous visit, the fortress was undergoing repairs; however, the fortress is normally one of the venues for the Montalcino wine and jazz festival, which takes place in the summer. Even if there are no events, you should visit if you can: the structure is impressive and there is a wine shop inside.

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3. Flying

The airport in Perugia closest to Montalcino is Perugia San Francesco d’Assisi Airport. To reach the city from the airport, all you need to do is take a bus or taxi.

It takes only approximately an hour and a half to travel to the town from here, and along the route, you will be able to take in breathtaking views of the beautiful Tuscan landscapes. Alternatively, you can take a public bus, which will take longer but is a more cost-effective option for budget tourists.

4. The Palazzo Pieri

The Pieri Palace, a former royal residence, is also associated with non-royal events. During the Italian War, from 1555 and 1559, the garrison deployed by the French emperor Henry II resided at this location. Their mission was to support the native soldiers of the region against those of Holy Roman Emperor Charles V. Today, it is a major tourist destination and home to a highly regarded wine market.

5. Atmosphere of Montalcino’s main piazza

The main square is one of the most attractive sites in Montalcino, located downhill from the citadel. The plaza contains everything a Medieval/Renaissance piazza would have: big spaces for crowds to gather and business deals to be made, a magnificent palace with a tower reminiscent of Siena’s Palazzo Vecchio, and a multitude of cafes and stores selling everything from souvenirs to snacks and wine. In the summer, the piazza transforms into a lovely outdoor venue for jazz concerts and wine sipping.

6. By Train

If you wish to reach Montalcino by train, there are approximately ten trains every day from Siena to the adjacent station of Buonconvento. Using the Grosseto line, this portion of the journey will take approximately 25 minutes.

After arriving in Buonconvento, you must board a bus that will transport you to Montalcino. Fortunately, the bus schedule generally coincides with train arrivals, so you will not have to wait too long.

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7. The wonders of Bibbiano Castle

Montalcino’s Bibbiano Castle is the best example of a castle one can hope to see in a historic European town. This ninth-century castle was constructed adjacent to Buonconvento and still looks robust and majestic today. Prior to being the property of the then-Cardinal Raffaello Petrucci, it was owned by two of Siena’s most illustrious families: the Guiglieschis and the Cacciacontis. It has had minor alterations since 850, but the majority of the old castle still stands.

8. Get lost in Montalcino’s narrow alleys

On the slope of a steep hill, crisscrossed by winding lanes, streets, and stairways, Montalcino develops.

They are an extravaganza of flowering balconies, patios, and small yards, and they occasionally open out to provide panoramic vistas of Val d’Orcia and the numerous Montalcino wines below. There is no right or wrong way to visit Montalcino; simply follow your intuition and you will not be disappointed!

9. By Bus

If you wish to ride the bus all the way to Montalcino, approximately 12 buses leave Siena for the town every day on a two-hour journey. Some buses travel directly to Montalcino, while others require a transfer at Buonconvento. Be sure to consult the schedule carefully and plan your travel accordingly.

10. The Museum Civico e Diocesano

As with most historic Italian cities, Montalcino has a deep connection to its religious past. This is best viewed at this diocesan museum, which has a number of significant works of art, including a triptych by Duccio. The museum is housed within the former convent of the neighboring Sant’Agostino Church.

11. Walk to Montalcino’s Duomo

The Duomo of Montalcino is situated in a privileged location in the city’s upper region. It was constructed between 1818 and 1832; however, it is composed of the same stone as the rest of the city and is a nice sight.

It is on our list of the greatest things to see in Montalcino largely due to its location, which overlooks a charming, tiny green space and provides a breathtaking panorama.

12. Ciacci Piccolomini d’Aragona

The Ciacci Piccolomini d’Aragona may be visited for just 12 EUR or 14 USD. Wine connoisseurs may opt to keep things simple and simply visit one of the many vineyards in the region. This is one of the greatest examples of a vineyard that cultivates the Brunello grape, and daily sampling excursions are available. For a few more euros, you can get a couple of bottles to accompany your dinner.

13. See Montalcino’s churches

In addition to the cathedral, Montalcino is home to a number of old churches, some of which are exquisite examples of Romanesque architecture, similar to those seen in nearby San Quirico.Notable ones include Sant’Egidio, San Francesco, and Sant’Agostino.

14. Visit La Fortezza

Visit La Fortezza, the town’s medieval fortification. Since the town’s four-year struggle for Florentine sovereignty, the monument has become a major symbol of civic pride and is currently regarded as one of the top attractions in Montalcino.

Given that La Fortezza holds such a special position in the hearts and identities of its residents, it should come as no surprise that it is one of the most popular tourist destinations. In addition, there are numerous wine-tasting establishments nearby as well as ample areas for children to explore. Consequently, you may savor the local wine as your children take advantage of the breathtaking surroundings.

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15. Cocco

On your own personal wine trail, you may wish to vary your selections slightly. The region is renowned for its full-bodied red wines, and Podere Il Cocco is the place to go if you wish to sample more. However, they also have wonderful white wines, and this is the ideal spot to experience their crisp organic Bianco, which has garnered recognition at artisanal wine fairs. Tours cost approximately 80 EUR (95 USD) and include a meal and wine samples.

16. Buy wine

Rosso di Montalcino and Brunello are world-renowned red wines produced in Montalcino (learn the difference here). The city is rife with wine businesses and winery tours are abundant. Even if you don’t drink, the sheer pride and enthusiasm in winemaking may cause you to fall in love with this city. Additionally, Montalcino wine makes an excellent gift for Italian food enthusiasts!

17. Benvenuto Brunello

The Benvenuto Brunello is the event in Montalcino that all wine connoisseurs should strive to attend. Every year in February, everyone gathers in the town center to celebrate the release of the new Brunello di Montalcino vintage.

As journalists, bloggers, sommeliers, influencers, and – of course – the general people converge to celebrate the upcoming good times (and wine), expect the atmosphere to be electric.

18. The Fortezza di Montalcino

Along with Bibbiano Castle, the Fortezza is one of Montalcino’s most important war-related remnants from Italy’s turbulent past. It is a massive, towering structure and the site of twice-yearly “contra de” competitions between the four regions of Montalcino (a generic name given to Italian city subdivisions). A stroll around the stronghold is definitely worth the time and effort, and if you haven’t seen enough wine to last you the entire vacation, there is also a winery on the premises.

19. Torneo D’apertura Delle Cacce

Torneo Apertura Delle Cacace, also known as the Opening of the Hunting Season, is an important date in the calendar of any Montalcino native. In August, the four neighborhoods of Borghetto, Travaglio, Ruga, and Pianello compete against one another in a crossbow competition in front of the castle.

Be prepared to witness the residents parading throughout the town in ornate medieval garb, wearing velvet robes, piebald tights, and intricate bodices. Of course, you will also be able to participate in folk dance in front of the main square.

Practical tips for visiting Montalcino

As a hilltop town still enclosed by its medieval walls, Montalcino is best approached by automobile and then explored on foot. Paid and free parking is accessible at multiple places outside the walls, some of which are pay-and-display. Please note that some parking spots are quite steep to access; if you choose one of these, make sure your vehicle can handle the incline!

We found the parking at the fortress to be the most convenient in terms of access to the rest of the city, as well as the easiest to access. Montalcino is one of the most steeply-sloped towns in the region, thus I strongly advise you to carry sturdy footwear.

The main town area surrounding the piazza posed minimal difficulty for any type of walker; however, you may want to avoid carrying a stroller if you are traveling to Montalcino with children due to the prevalence of cobblestones and steps. We visited Montalcino with our children, and they enjoyed it. However, we were unable to locate a playground for them, so although we do recommend a visit, we wouldn’t recommend it as a base for seeing Tuscany with children.


Montalcino is without a doubt one of the most beautiful towns in Tuscany and a terrific spot to visit on your Italian trip since it is a magical wonderland of brilliant medieval architecture and world-famous wines. This extraordinary Tuscany town is home to some of the most known red wines in the region, but it has so much more to offer than just fine beverages.

There is something for everyone in this fascinating region of the world, which features spectacular clocks, breathtaking abbeys, a busy town center, and an abundance of fantastic events held throughout the year.

If you’re planning a vacation to Tuscany and want to explore enchanting cities like Montalcino, contact Italy4Real and chat with a member of our staff for specialized advice and assistance in creating a tailor-made tour.

Frequently Asked Questions(FAQ) about Best Things to Do in Montalcino

What is Montalcino known for?

In Tuscany, Italy, Montalcino is a magnificent ancient town set on a hilltop. The town is renowned for the production of two renowned Tuscan wines, Rosso and Brunello di Montalcino, and is a beautiful day trip destination.

What is the difference between Montalcino and Montepulciano?

In Montepulciano, a minimum of 70% Sangiovese is required for both the Vino Nobile and the Rosso. In contrast, Montalcino’s reds are 100% Sangiovese. Other approved grape varieties are Canaiolo (up to 20 percent), Colorino, and Mammolo.

What is Pienza Italy known for?

Pienza is renowned for its native pecorino sheep’s milk cheese, which can be sampled and purchased in many of the town’s small shops. Depending on the age and intensity of the cheese, it is utilized in a variety of regional recipes.

Is Montalcino al Chianti?

Chianti and Chianti Classico are produced from the sangiovese grape, whereas Brunello is produced from a superior clone of sangiovese, properly known as sangiovese grosso.

Is it worth going to Montepulciano?

If you have a car, Montepulciano is a lovely destination for a day trip and an ideal base for exploring Tuscany. It is one of the most charming and lovely towns in all of Tuscany, and we strongly advise you to visit.

Is Montepulciano a touristy?

Due to its exceptional vineyards, the Montepulciano region is regarded as one of the world’s finest winemaking districts, making it one of the most popular and frequented tourist sites in Tuscany.

How much time do you need in Montepulciano?

On the other side, the town is small and may be explored in an hour or two. On the other hand, Montepulciano is a much larger town, and the ascent to the summit is a long and pleasant walk. It will take half a day, and is also worth rewriting, but that’s up to you and your time schedule.

What food is Montepulciano known for?

Therefore, to begin lunch or supper, it is essential to serve local specialties such as pecorino di Pienza DOP with Cinta Senese ham DOP, or wild Tuscan pork and Chianina beef IGP salami and bresaola.

What do you drink in Montepulciano?

Montepulciano is a fantastic wine to combine with savory and robust meat dishes as the wine’s tannic character and acidity cut through fats. Try pairing it with beef bolognese, brisket, meatloaf, barbeque, and hamburgers, in addition to any dish with a rich tomato-based or cheese sauce. (Perhaps even sausage with fondue?

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