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Montalcino in Italy, a wine lovers must-visit destination

Montalcino in Italy, a wine lovers must-visit destination

Famous for its world-renowned Brunello, Montalcino in Italy, is a must-visit destination for all wine lovers. This charming medieval hill town, surrounded by vineyards, wineries and oak forest overlooks the also famous Val d’Orcia. 

From its fortress and defensive walls to its churches and steep streets, Montalcino is home to a thousand years of rich history steeped in conflict, and is a delight to explore.

Traditional Tuscan food is available throughout this picturesque town, and visiting an enoteca (wine bar) or two is highly recommended.

You only need suitable walking shoes and a good appetite, so why not come for the wine then stay for the food and medieval history?

Is Montalcino in Italy worth visiting?

Montalcino in Italy is definitely worth visiting! Here are five reasons why:

1. The scenery is absolutely stunning – from the rolling hills to the steep medieval streets, there’s something for everyone to enjoy.

2. The food and wine scene is world-class – whether you’re looking for a Michelin-starred meal

 or a casual trattoria Montalcino has it all, matched every inch of the way with world-renowned wines.

3. The history is fascinating – from the Etruscans to the Medici, Montalcino has been central to some of Tuscany’s most important historical events.

4. The culture is rich and vibrant – from traditional events to contemporary jazz festivals, Montalcino has something to offer everyone.

5. The people are warm and welcoming – from the locals to the tourists, Montalcino is a place where everyone feels at home.

So, if you’re looking for a place to relax, enjoy good food and wine, and soak up some history and culture, Montalcino is most definitely worth visiting!

What does Montalcino mean in Italian?

The name Montalcino is thought to be derived from the Latin words ‘mons ilcinus’ meaning ‘mountain of holm-oak’. Forests of holm oak still partly surround Montalcino today.

Parked vespa
Vespa parked in Montalcino

What is Montalcino wine?

Montalcino wine is a type of Italian red wine that is produced in the Montalcino region of Tuscany. The wine is made from a variety of the Sangiovese grape and is known for its fruity and floral flavor profile. Montalcino wines are typically full-bodied with moderate tannins and acidity.

Montalcino wines are typically classified as DOCG ( Denominazione di Origine Controllata e Garantita) wines, which is the highest quality designation given to Italian wines. There are four main types of Montalcino wines: Rosso di Montalcino, Brunello di Montalcino, Riserva, and Sant’Antimo which can also be white wine.

What is the difference between Montalcino and Montepulciano?

Both Montalcino and Montepulciano are located in the province of Siena, Tuscany, Italy and share many similarities. Both are medieval hill towns with defensive walls, steep streets and are renowned for their wine.

However, Montepulciano was consistently aligned with Florence and received handsome rewards for it. Under the rule of Siena, Montalcino tried to change allegiance to Florence, and was punished severely for it by Siena. 

As a consequence Montepulciano grew and flourished, until Montalcino finally came under the control of Florence. The importance of Montepulciano then declined.

What we see today are two medieval towns that present very differently. Montepulciano is larger with more people, restaurants and shops, whereas Montalcino is more open and feels more genuine to its medieval origins.

Driving to Montalcino, Italy.

Montalcino is situated about 120 km south of Florence and about 40 km southeast of Siena. Arriving by car is by far the most popular, flexible and quickest solution, unless you are part of an arranged tour.

The parking lot down the minor road opposite to the Fortress is recommended. There is ample free parking available, or paid parking amongst the painted blue lines. There is also a toilet available, next to the walkway that takes you up toward the Fortress.

Montalcino is a great place to stay as you drive about doing day tours. You’ll be able to experience the wine country and make your way through some of Italy’s most famous vineyards while taking in stunning views that will leave lasting impressions on everything within eyesight!

Let’s walk


Let’s begin our walk at the famous fortress that never fell, even under extreme attack! 

The current version of the Fortress of Montalcino was built in 1361, after Siena defeated Montalcino in battle. The Palazzo dei Priori was built at the same time, as the Sienese asserted their dominance.

After restoration last century, the fortress remains mostly intact and still houses the medieval chapel. 

Concerts and special events such as the famous Jazz and Wine in Montalcino festival are held here, and there is also an enoteca (wine store). 

Tickets can be purchased to climb the walls and access the walkways and towers. The annual Sagra del Tordo (feast of the Thrush) takes place here on the last Sunday of October, in association with the longbow competition on the playing field between the quartieri (more on them below…).

Fortress in Montalcino

Leaving the fortress, wander north into the pedestrian Via Ricasoli. Passing tempting food and wine shops, pause for a nice ‘selfie’ with the ramparts of the fortress rising above the medieval street behind you. 

Continue across Via Bolorini to where on Fridays you will find the stalls of the weekly market. As you arrive at Palazzo Pieri, further along, on the left, you can enter the courtyard to find a nice bar with a simple menu.

A garrison was stationed here from 1555 to 1559, commanded by Blaise de Monluc, a brutal but effective commander. Sent by King of France Henry II in aid of the “Republic of Siena in Montalcino”, the garrison withdrew when the King relinquished Montalcino.

This prestigious Palazzo then became the home for nobility before coming into the hands of the citizens after World War I.

The Communist Party firmly established itself here before it transitioned into a friendly local meeting place. In the warm evenings of summer the elderly played endless card games over coffee, and the young people entertained themselves on the billiard tables.

Museo Civico e Diocesano

On the corner opposite is the 14th century Gothic-style Romanesque church Sant’Agostino with the former convent attached.

The church is a basic hall layout with wonderful stained glass windows and 14th and 15th-century frescoes depicting the Passion of Christ and Life of St Anthony Abbot

The former convent next door has two museums. The Civic Museum houses a collection of works from the medieval and Renaissance periods. Featured is a wooden crucifix from the Sienese school, two 15th-century wooden sculptures, and several terracotta sculptures from the Della Robbia school. The Diocesan Museum, on the other hand, contains a collection of religious artefacts from the same time period.

Chiesa di Sant’Agostino
Chiesa di Sant’Agostino

Cathedral of the Holy Saviour

Continue up the hill veering to the left at the bishop’s palace along Via Spagni towards Cattedrale del San Salvatore. In front of the cathedral is a nice little lawned area offering far reaching views over medieval rooftops.

Previously rebuilt in the 14th century, the 1832 Neoclassical version is built on the original site dating back to 1000 AD. It was designated a cathedral in 1462 by Pope Pius II, the same year as the completion of his own cathedral in Pienza.

Inside are several works of art from the second iteration of the church. Francesco Vanni’s 1588 ‘Immaculate Conception with the Child Jesus and God the Father’ most notable for its religious symbolism. 

Mother Mary with Baby Jesus

To begin, the virgin Mary steps on the head of the dragon, the emblem of Satan; 

the moon beneath her feet, a nuptial symbol since she is the divine Bride; 

in the lower right corner we see the “spotless mirror”, a reference to her Immaculate Conception; 

the white lily, the emblem of purity; 

on the left is the mystic rose, that implies she is Queen of God’s garden, which is the universe He created; 

the spring, symbol of life; 

the “sealed fountain”, symbol of divine motherhood; 

the temple of the Holy Spirit, of which she was the instrument and dwelling place; 

the “enclosed garden”, a sign of her virginity; 

the tower of David, a reference to Mary’s fortitude; 

the stairway to Paradise and the door of Heaven, in that she is the path of access to her Son; 

the crown of twelve stars, a reference to the twelve tribes of God’s people; 

the morning star, since Mary in her holiness is the first fruit of Christ’s salvation; 

and the Trinitarian symbolism: Mary holds her Son, conceived at the behest of the Father through the Holy Spirit.

Historic carvings in stone
Medieval travertine carvings

In the Baptistry chapel, there is a reconstruction of medieval travertine carvings, thought to be from the original church portal. At top, the Fleur-de-lys a symbol for the Blessed Virgin Mary. Then Christ imparting his blessing with two angels. Then the four Evangelists, and lastly a lion and a dragon both punishing sinners.

Down past the gardens

Leaving the cathedral, walk straight ahead down the steps along Costa Spagni as it dives through the middle of the community. The garden spaces you see are original medieval growing plots. Watch out for cars as you cross Via Cialdini, enjoying the distant views of the Val d’Orcia landscape. Turn left, then right at Via Giuseppe Mazzini, to descend the steps of Scale di Via Moglio.

Half way down the steps, turn right at Via delle Scuole and walk some 100 meters until the road ends. To your right, climb up the covered steps of Vicolo delle Scuole to Via Giacomo Matteotti.

Descending medieval street
Steep street in Montalcino

Palazzo dei Priori

At the top, to your right, you’ll find yourself a few steps away from Piazza del Popolo. Directly opposite is the Palazzo dei Priori. In the loggia just to your right is a statue of Cosimo I de’ Medici, Grand Duke of Tuscany. 

Heraldic coats of arms of noble families are mounted below the Medici’s on the facade that fronts the piazza. They belong to the Priors (the mayors) who were inserted by Siena, to ensure rebellion didn’t grow among the people.

Around the other side of the building there are more coats of arms. And also a column topped by the she-wolf feeding Romulus and Remus – an artefact of when Siena owned this town.


Montalcino in Italy is divided, like many medieval cities, into quarters called contrade, Borghetto (hamlet), Travaglio (labour), Pianello (a strip of land that runs between two rows of vines) and Ruga (wrinkle), each with their own colors, songs and separate drum rhythms to distinguish them.

Twice each year they meet for the Sagra del Tordo in a breathtaking archery contest under the walls of the Fortezza. Conducted in Medieval dress, with lords and ladies of each contrada who accompany the proceedings.

However, throughout the year many intimate events are organised which keep the fraternities closely bonded and helps to maintain the civic pride that is apparent in this wonderful medieval town.

Ape parked in Montalcino
Working vehicle parked in town

History of Montalcino in Italy.

Montalcino is located high on a hill between the Val d’Orcia and the Ombrome valley, but is considered a part of the Val d’Orcia. Either way, the views across the beautiful valleys and up to Siena are as captivating as they are far-reaching.

When you talk about Montalcino in Italy your mind is immediately cast toward Brunello, one of the most famous Italian wines. But it hasn’t always been that way; while Brunello di Montalcino has been produced since the 1860’s it wasn’t until after the war in the mid 1940’s that its amazing aging capacity became widely known. 

While good wine has been made here for some time, historically Montalcino is famous for its fine leather goods and ceramics.

The name Montalcino is thought to be derived from the Latin words ‘mons ilcinus’ meaning ‘mountain of holm-oak’; where forests still survive to this day. For several hundred years the village was under the jurisdiction of the nearby Abbey of Sant’ Antimo, who directed the establishment of a community here. A huge amount of effort went into terracing the steep Western slope to create productive orchards.

Many refugees from the Saracen-annihilated Etruscan/Roman town of Roselle settled here. But as the Abbey’s power diminished following siege after siege by Siena, Montalcino was surrendered.

For centuries after, fierce fighting by the City-States of Florence and Siena scarcely gave Montalcino an opportunity to develop its own power. Historically Montalcino is most commonly associated as being ruled by Siena, but it was a love/hate relationship.

After Montalcino supported the ill-fated Florence in the nearby Battle of Montaperti in 1260, the victorious Siena devastated Montalcino. By destroying buildings and farms alike, the hill town was committed to a century of servitude.

Podeste family crests
Centuries old family crests