Best Things to Do in Montalcino
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Montalcino is a charming little utopia on top of a hill in the province of Siena. It is a great place to go if you want to try some of Tuscany’s world-famous red wine. Imagine a charming little town with charming cobblestone streets, stunning views of the valley around it, a fascinating medieval fortress, and, of course, a great wine scene. In this article, you can learn about the best things to do in Montalcino.

Montalcino is one of the best towns in Italy for wine lovers. It is famous for being the birthplace of Brunello di Montalcino, red wine with flavors and hints of coffee that is known all over the world. The famous wine played a big part in making the town what it is today, and there are many vineyards and wineries nearby where visitors can try it.

But Montalcino isn’t just a popular place for people who like wine. From archery competitions to world-class wineries, this amazing town in Tuscany has a lot to offer.

If you’re already in love with Montalcino but want to know more about it before you go, we’ve put together some important facts that will help you plan the most memorable trip.

The 20 Best Things to Do in Montalcino

1. The Abbey of Saint Antimo

This abbey was built before the year 814. It is thought that it got its name from the saint Anthimus. It’s not clear exactly when, but old records show that it was there at that time. From then on, the abbey became the center of the town. Now, it is one of Italy’s oldest abbeys that is still in use and a beautiful place to visit. A short drive from Montalcino, the abbey plays the sounds of Gregorian chanting, which was left over from when French monks were there. At certain times, visitors can go inside the church.

2. Admire Montalcino Rocca

Montalcino’s fortress, which sits on top of the hill where the town is, is the most prominent building on the skyline. The fortress was built in 1361 when nearby Siena took control of Montalcino. It is still a strong sight.

Tall walls and turrets are still standing, and they look mostly the same as they did when they were built. When we were there last, the fortress was being fixed up. In normal times, though, it is one of the places where the Montalcino wine and jazz festival takes place every summer in town.

Even if there are no events, you should walk in if you can because the building is impressive and there is a wine shop inside.

3. Flight

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Perugia San Francesco d’Assisi Airport in Perugia is the closest airport to Montalcino. From the airport, all you have to do to get to the town is take a bus or taxi.

From here, it only takes about an hour and a half to drive to the town, and along the way, you can see some of the most beautiful parts of Tuscany. You can also take a public bus, which will take longer but is better for people on a tight budget.

4. The Palazzo Pieri

The Pieri Palace was once a place where kings and queens stayed. It also has some history that has nothing to do with royalty. During the Italian War, from 1555 to 1559, Henry II, the French emperor, sent a French garrison to stay here. Their job was to help the local forces fight against the forces of Charles V, the Holy Roman Emperor. It is now a popular place for tourists and the site of a well-liked wine market.

5. Atmosphere of Montalcino’s main piazza

The main square, which is downhill from the fortress, is one of the most beautiful places in Montalcino.

The piazza has everything you’d expect from a Medieval or Renaissance square: lots of room for crowds to gather and trade deals to be made, a beautiful palazzo with a tower that looks like the tower of Palazzo Vecchio in Siena, and lots of cafes and shops selling everything from souvenirs to snacks and wine.

During the summer, the piazza turns into a beautiful outdoor space where jazz concerts and wine tastings take place.

6. By Train

If you want to take a train trip to get to Montalcino, Siena has about ten trains a day that goes to the nearby station of Buonconvento. This part of the trip takes about 25 minutes on the Grosseto line.

When you get to Buonconvento, you’ll have to take a bus to Montalcino. Luckily, the bus schedule usually matches up with when the train arrives, so you won’t have to wait too long.

7. What Bibbiano Castle has to offer

When you go to an old town in Europe, you can usually find at least one castle. The best castle in Montalcino is Bibbiano Castle. This fortification was built in the 9th century and is close to Buonconvento.

8. Get lost in the small streets of Montalcino

Montalcino is built on the side of a steep hill, where there are many winding streets, alleys, and stairs.

Most of the time, cars aren’t allowed on them, but when they do open up, they offer sweeping views of Val d’Orcia and the many wineries in Montalcino below.

There is no right or wrong way to visit Montalcino. All you need to do is go with your gut, and you won’t be let down.

9. By Bus

If you want to go all the way to Montalcino by bus, about 12 buses leave Siena for the town every day. The trip takes about two hours. Some buses will take you straight to Montalcino, while others will make you change at Buonconvento. So, pay close attention to the schedule and plan your trip accordingly.

10. The Museum Civico e Diocesano

Like most old Italian cities, Montalcino has a strong connection to its religious past. This is best seen at the diocesan museum, which has a triptych by Duccio and other very important works of art. The museum is set up in the old convent of the Chiesa di Sant’Agostino church, which is close by.

11. Walk to Montalcino’s Duomo

The Duomo of Montalcino is in a great spot in the higher part of the city. It was built between 1818 and 1832, so it is fairly new. However, it is made of the same kind of stone as the rest of the city, and it is a nice place to visit.

It faces a beautiful small green area and has a great panoramic view, which is mainly why it’s on our list of the best things to see in Montalcino.

12. Ciacci Piccolomini d’Aragona

Wine lovers may prefer to keep things simple and just visit one of the many vineyards in the area. For example, the Ciacci Piccolomini d’Aragona costs only 12 EUR or 14 USD to visit. This is one of the best vineyards that grow the Brunello grape, and you can take tours and taste the wine every day. You can get a couple of bottles to go with your dinner for a few euros more.

13. Visit the churches in Montalcino

As well as the duomo, Montalcino has a number of old churches. Some of them are in a beautiful Romanesque style, like the churches in nearby San Quirico. Sant’Egidio, San Francesco, and Sant’Agostino are three that stand out.

14. Visit La Fortezza

Visit La Fortezza, a medieval fortress in the town. Since the town fought against the Florentine rule for four years, the monument has become an important symbol of town pride. It is now known as one of the best things to see in Montalcino.

La Fortezza is usually at the top of every tourist’s list because it is so important to the people who live there and to their sense of who they are. Also, there are a lot of places nearby where you can stop for a wine tasting and a lot of space for the kids to play. So you can enjoy the local wine while the kids play in the beautiful scenery.

15. Cocco

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Lastly, you might want to change things up a bit on your own little wine trail. The area is known for its full-bodied red wines, which you can get at Podere Il Cocco if you want to try more. But they also have great white wines, and this is the perfect place to try their crisp organic Bianco, which has been getting attention at artisanal wine fairs. Tours cost between 80 EUR and 95 USD and include tastings of food and wine.

16. Buy wine

Rosso di Montalcino and Brunello, two red wines from Montalcino, are known and loved all over the world (learn the difference here). There are many wine shops in the city, and there are many wineries to visit.

If you love wine, this is a great place to be because people here know a lot about it, are passionate about it, and make great wine. But even if you don’t drink, the pride and interest in making wine might make you love this town.

Also, Montalcino wine is a great gift for people who like Italian food.

17. Benvenuto Brunello

For all of you who like wine, the Benvenuto Brunello is the event in Montalcino that you should try to see. Every February, people gather in the town center to celebrate the release of the new Brunello di Montalcino vintage.

Expect the air to be buzzing with excitement as journalists, bloggers, sommeliers, influencers, and, of course, the general public gathers to celebrate the good times (and wine) to come.

18. The Fortezza di Montalcino

Along with the Bibbiano Castle, the Fortezza is one of the most important reminders of Italy’s long history of war. It’s a big, impressive building that is used twice a year for “contra de,” which are competitions between the four parts of Montalcino (a generic name given to Italian city subdivisions). The time and effort it takes to walk around the fortress are well worth it. If you haven’t seen enough wine to last you the whole holiday, there is also a winery on site.

19. Torneo D’apertura Delle Cacce

The Torneo Apertura Delle Cacace, or the Opening of the Hunting Season, is a big deal for anyone who lives in Montalcino. It’s a bit of a warm-up for the Sagra del Tordo. A crossbow competition between the town’s four neighborhoods, Borghetto, Travaglio, Ruga, and Pianello, is held in August in front of the fortress.

Get ready to see people walking around town in velvet robes, piebald tights, and elaborate bodices. They will be dressed like they are from the Middle Ages. Folk dancing will be going on in front of the main square, so you can join in if you want to.

20. Advice on how to get around Montalcino

Montalcino is a town on a hill that is still surrounded by the walls it had in the Middle Ages. Because of this, it is best to drive to Montalcino and then explore it on foot.

There are several places outside the walls where you can park for free or for a fee. Some parking spots are hard to get to because they are up a steep hill. If you choose one of these, make sure your car can handle it. We found that parking at the fortress was the easiest and best way to get to other parts of the city.

Montalcino is one of the steepest towns in the area, so if you want to get around, you should bring good walking shoes.

The main part of town around the piazza was easy to walk through for anyone. If you are coming to Montalcino with kids, though, you might not want to bring a stroller because there are a lot of cobblestones and steps.

We took our kids to Montalcino, and they liked it. However, we couldn’t find a good playground for them, so this wouldn’t be our first choice as a place to stay if we were taking kids to Tuscany.


Montalcino is one of the most beautiful towns in Tuscany and a great place to visit on your trip to Italy. It has beautiful medieval buildings and wines that are known all over the world. Even though the high-quality drinks might be enough to draw you in, this beautiful town in Tuscany has so much more to offer than just some of the most famous red wines in the area.

This beautiful part of the world has something for everyone. There are amazing clocks, beautiful abbeys, a busy town center, and lots of great events going on all year long.

If you want to visit magical towns like Montalcino on a trip to Tuscany, contact Italy4Real and talk to a member of our team to get personalized advice and help planning a trip just for you.

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

What makes Montalcino famous?

Montalcino is a beautiful, old town in Tuscany, Italy, that sits on top of a hill. The famous Rosso and Brunello di Montalcino wines are made in this town, which is also a great place to spend a day in Tuscany.

What makes Montalcino different from Montepulciano?

In Montalcino, all of the red wines are made from Sangiovese, but in Montepulciano, both the Vino Nobile and the Rosso must have at least 70% Sangiovese. Canaiolo (up to 20%), Colorino, and Mammolo are the other types of grapes that can be used.

What do people know about Pienza, Italy?

Pienza is known for its pecorino cheese, which is made from sheep’s milk. You can try it and buy it at many of the small shops in the town. The firm cheese is aged for 6 to 18 months. Depending on how old it is and how strong it is, it is used in many local dishes.

Is Montalcino al Chianti?

Sangiovese is the grape used to make Chianti and Chianti Classico. Brunello, which is a better clone of Sangiovese, is used to make the wines of Montalcino, which is why it is called Sangiovese Grosso.

Does it make sense to go to Montepulciano?

Montepulciano is a great place for a day trip and a great place to stay if you have a car and want to see more of Tuscany. It is one of the nicest and most beautiful towns in all of Tuscany, and we really think you should go there.

Is Montepulciano full of tourists?

Because of its great vineyards, the area around Montepulciano is thought to be one of the best places in the world to make wine. This makes it one of the most popular tourist spots in Tuscany.

How long do you have to spend in Montepulciano?

On the other hand, it’s a small town that you can see in an hour or two. On the other hand, Montepulciano is a much bigger town, and getting to the top is a long but pleasant walk. It will take a half day and is also worth going over again, but that depends on your schedule.

What food is famous in Montepulciano?

So, for lunch or dinner, you should start with local products from around Montepulciano, like pecorino di Pienza DOP with Cinta Senese ham DOP or wild Tuscan pork and Chianina beef IGP salami and bresaola.

What drinks do people in Montepulciano drink?

Montepulciano goes well with rich, savory meat dishes because the wine’s tannins and acidity cut through the fat. Serve it with beef bolognese, brisket, meatloaf, barbecue, hamburgers, and any dish with a rich tomato-based or cheese sauce. (Perhaps even sausage with the fondue?