Things to Do in Montalcino, Tuscany

Another Tuscan town commonly associated with wine is Montalcino, the homeland of the famous Brunello wine.  Its original recipe dates back to 1888 when Ferruccio Biondi Santi started to grow only one grape variety named Sangiovese to make a brand-new kind of wine.

Tuscan winemakers usually mixed several grapes, but he thought selecting only one was the best option to produce an original wine. Brunello wine has to age for at least five years (and two inside oak barrels!) before being ready for consumption.

Like many other Tuscan towns near Siena, Montalcino looks like a medieval settlement dominated by a fortress and surrounded by walls, vineyards, and hills. It’s been perfectly preserved throughout the centuries, so it’s a picturesque and scenic location, perfect for your pictures!

Here’s a list of what you can see and do in Montalcino:

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18 Things to Do in Montalcino

Enjoy a wine tour and taste a glass of Brunello wine

The most popular activity in Montalcino is wine tasting! There are several themed tours available at Montalcino Wine Tours: Private and Group Tours in Tuscany and Italy: tastings, hikes, guided visits, and so on will make you feel spoilt for choice!

Stop in Piazza del Popolo

The main square is the perfect place to start exploring Montalcino. You’ll find the main public buildings, a picturesque and cozy atmosphere, and a few restaurants and cafés for a pleasant stop.

Take a look at Palazzo dei Priori

Palazzo dei Priori has been the Town Hall for centuries. Its majestic stone façade and its crenelated tower make it one of the main landmarks of Montalcino. Take a look at the statue of Cosimo de Medici just below the tower.

Enter the Cathedral

The Cathedral of the Holy Savior was built in the 15th century upon the remains of an older church in Romanesque style. Together with the fortress, it’s the highest building in town, and it can be spotted from a distance.

Its neoclassical façade is rather simple in comparison to its internal decorations, among which you cannot miss the paintings of some famous local artists like Francesco Nasini and Francesco Vanni.

Walk on the castle’s ramparts.

The local fortress named “Rocca” is one of the main attractions of Montalcino and the whole Orcia Valley. It was built in the 14th century as a military outpost, and its elevated position gave it an essential role in defense of the area for centuries. You can enter from Cassero Gate and step inside the internal courtyard surrounded by the original walls.

Today, you can still visit the chapel, the armory, and only a couple of rooms, but you can still access the ramparts and enjoy the view! Several events take place in the courtyard during summer, and a winery has its headquarters right there all year long! You can access the courtyard and the garden for free, while the cost to access the ramparts is 4 euros. For more information, check here.

Visit the Civic Museum

The museum is housed inside a former monastery dating back to the 15th century and is located next to the church of the Saints Philippe and James. It was restored in 1977 to create an exhibition space displaying several examples of religious art.

There’s also a room entirely dedicated to local painters and some beautiful wood carvings dating back to the Middle Ages. In 2021 a new section was created to display the history of the main local wine: it’s called the “Temple of Brunello,” and it engages the visitors through an immersive experience. For more information, click here.

Attend the Jazz & Wine Festival

A summer festival takes place in July featuring the best national and international jazz musicians. Other than for its music, it’s very much appreciated thanks to its gastronomic stalls and its wine tastings! For more information, click here.

Have a day trip to Bagno Vignoni.

This lovely town is located only 18 km away from Montalcino, and it’s been a famous spa town since the Roman era. One of its highlights is the huge thermal basin located in the main square, which was a great attraction in the past. Now it’s forbidden to take a bath there, but it’s a scenic place to take some pictures! If you’re up for a spa day, take a pleasant walk outside the town and reach the old Roman baths immersed in nature!

Rent a bike

Montalcino is a great destination for bike lovers, and there are several bike trails in the countryside to keep you active and busy. You can freely wander around or take the famous cycle path named “L’Eroica,” which spans 153 Km in the Chianti area and the Orcia Valley! It’s split into 12 sections that can be completed in 1 or 2 days. For more information, click here.

Visit the Abbey of S. Antimo

You can easily reach this picturesque abbey in the countryside by bike from Montalcino. It’s a medieval architectural masterpiece and a very spiritual and quiet place where you can still listen to the monks singing the Gregorian chants. Legend has it that it was built by Charlemagne in 781.

It is said that he was going back home after a visit to Rome when a mysterious disease hit his army, failing to kill his soldiers. They stopped right there, and an Angel appeared to Charlemagne, telling him to make some herbal tea with local grass and give it to his soldiers. They were all healed in the end, and Charlemagne wanted to erect a church to celebrate that miracle.

Take plenty of pictures.

If you want to take some Insta-friendly pictures, Montalcino is the perfect spot! Just head to the small park beside the Church of the Madonna del Soccorso, climb up to the ramparts, or enter the town from Cervara gate to take in the best views!

Attend a show at Teatro degli Astrusi

Astrusi Academy is a theater company that was established in Montalcino in the XVII century. Its theater was restored in the 18th century, and it was turned into a masterpiece thanks to its ceiling representing Apollo’s chariot and the seven Muses. It’s a small theater, only accommodating 700 people, but it’s still very popular among locals. More information at Montalcino Teatro

Enter the courtyard of Pieri Palace.

It’s hidden from the street, and not many visitors notice it, but it’s a great example of Renaissance architecture. It was the military headquarters of the French army between 1555 and 1559, and it was later used by the Medici family to control the town. The Palace houses a popular social club.

Plan a special event at Banfi Castle.

It’s a privately owned castle that was converted into a winery, a hotel, and a restaurant. Its amazing location among the vineyards makes it a very popular place for parties, weddings, and special events. For more information, click here.

Visit the cellar of Romitorio Castle.

Another famous wine estate is Romitorio castle, just outside Montalcino. It’s been active in the wine sector since the 80s, and it’s specialized in growing the Sangiovese grape variety. Their cellar is open to visitors, and it’s a sort of museum where nature, culture, and wine are mixed together to offer an original experience. More information at Castello Romitorio

Enjoy some hikes in nature.

There are several hiking trails near Montalcino, and one of the best trails goes up to the Abbey of S. Antimo. It’s a 10 km long path, but it’s pretty easy, winding through olive trees, vineyards, and forests.

Have a day trip to San Quirico d’Orcia

Another lovely destination near Montalcino is San Quirico d’Orcia which is also easily reachable by bike. It’s a great sightseeing destination since it’s full of churches and historical buildings despite being rather small. You can spend a couple of hours exploring the village and then cycle on to reach the spectacular Chapel of Vitaleta with its iconic cypress trees.

Attend the Festival of the Thrush

This ancient tradition marked the start of the hunting season, and it still takes place on the last weekend of October. In modern times, the main event has become an archery competition where the winner gets a silver arrow. There is also a parade of costume characters, other than lots of food and wine, of course! More information at Sagra del tordo

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