Montalcino is mostly mentioned in referenced to the famous wine, Brunello di Montalcino. Though a day trip to this little medieval town would not be complete without trying this red in a winery or restaurant, there are many other things to do. The slow pace of Montalcino invites visitors to embrace the Italian dolce vita: take your time, enjoy a stroll through the historical center, visit the fortress and churches and taste the locally made pecorino cheese.

One of Val d’Orcia’s Jewels

The landscape of Val d'Orcia from Montalcino
Montalcino is atop a hill from where you can admire the Val d’Orcia landscape.

The beautiful Val d’Orcia landscape frames the town of Montalcino. It is a short drive away from Pienza and about 50 minutes South of Siena. Montalcino is on top of a hill, which gives it amazing views from every side. The center has maintained a very Medieval appearance, almost as though time has come to a standstill. Most narrow streets are at an incline, so be ready to traipse up and down.

The entrance to the Rocca of Montalcino
The entrance to the fortress of Montalcino with its powerful ramparts. The double arched entrance is a reminder that the fortress was founded by Siena.

The fortress sits at the top of Montalcino and dates back to the 14th century. Cosimo I ordered the construction of its spectacular ramparts in 1571. When Siena fell to Florence in 1555, many Sienese rebels sought refuge in Montalcino. The Second Republic of Siena in Montalcino lasted four years until Cosimo I finally won and the town got incorporated in the Grand Duchy of Tuscany under Medici rule. Still today, in remembrance of Montalcino’s unwavering support, the town’s standard bearer has pride of place at the Palio di Siena.

Things to do in Montalcino

If you happen to be in Val d’Orcia, you would be remiss not to make a stop in Montalcino. After visiting the town’s most famous landmarks, end your day at a local restaurant with a bottle of Brunello and a selection of Tuscan cheeses while the sun sets and makes the Val d’Orcia hills glow.

The Florentine tour operator I Just Drive organises a private or shared guided tours to Montalcino that will also take you to the other gem of Val d’Orcia, Montepulciano.

Without further ado, here are the top things to do in Montalcino.

The fortress

Landscape of Val d'Orcia from the top of the Montalcino fortress walls
Walk around the the walls of Montalcino’s fortress and enjoy views of a beautiful landscape.

Montalcino’s fortress is very well conserved. Walk around the perimeter of the ramparts and take in the incredible views.

Wine lovers will be happy to hear that they can pair this cultural activity with a wine tasting in the enoteca of the fortress. Though a little pricey, the wine restaurant has an incredible selection and an unforgettable backdrop.

If you happen to be in Tuscany in July, you’ll be able to see the city transform for its annual Jazz and Wine Festival.

History fans might want to come during the last weekend of October to witness the Sagra del Tordo. This medieval festival gives Montalcino’s four neighbourhoods the chance to face off in an archery tournament (medieval costume de rigueur!).

Medieval festivals can be found all over Tuscany and are a great way to immerse yourself in the region’s rich and tumultuous history.

The churches

The church of Saint Augustin in Montalcino view from far
If you don’t have much time, the church of Sant’Agostino is worth a visit.

There are around 9 churches to choose from in Montalcino. If you can visit only one, head to the Church of Sant’Agostino in Via Ricasoli,1. This 14th century building in gothic style hosts a painting attributed to the famous Sienese painter Bartolo di Fredi. The adjoining monastery has two beautiful cloisters.

Compare Sant’Agostino to the town’s cathedral, San Salvatore. Originally built around the same period, it was torn down and rebuilt in the neoclassical style in the first half of the 19th century.

The Palazzo dei Priori

Palazzo dei Priori in Montalcino
Like many Medieval towns of Tuscany, Montalcino had its town hall where the city authorities were located.

Every Medieval town in Tuscany had a building for its governing body. Palazzo dei Priori, in Montalcino’s main square, Piazza del Popolo, held that function until it became the city’s town hall. Its construction spanned over the end of the 13th century and the beginning of the 14th.

The stone facade and clock tower are decorated with marble renditions of Montalcino’s ruling families’ coat of arms.

On the left of the Palazzo dei Priori, there is a 15th century loggia with seven arches.

Give your legs a rest at the café-restaurant Alle Logge di Piazza and admire the square.

The Civic and Diocesan Museum

Simone Martini fresc
This Simone Martini fresco gives you an idea of what the Sienese style of painting is like.

Immerse yourself in the sacred and lay art of the area from the Middle Ages to the 20th century in the Museo di Arte Civico e Diocesano. The exhibit is displayed in the ex-convent of Sant’Agostino  in Via Ricasoli, 31. You will find masterpieces of the Sienese school as well as religious artefacts and even an archeological exhibit in the basement. The ticket, which includes a stroll around the battlements of the fortress, costs € 6.

Brunello wine

A wine cellar in Montalcino with modern fermentation barrels
While in Montalcino, include a visit to a wine producer. Wine tastings are usually included!

A visit to Montalcino must include a taste of Brunello. The town is inundated with wine shops and enoteche (restaurants specialising in wines) so you will definitely have many options to choose from.

Brunello is one of the most popular Tuscan and Italian reds. The wine as we know it today was invented by the Biondi Santi family in the 19th century, even though wine has been produced in the area for centuries. If you would like to know more about this local beverage, visit the Brunello Museum in the Barbi vineyard. The exhibit covers the daily life of the people of Montalcino before the invention of Brunello and also how the wine is made. The museum closes on wednesdays.

Montalcino can be a stop on a wine tasting tour or just a day trip to explore the peaceful pace of the Italian small town. Architectural beauty and culture can be found all around Tuscany, even in its villages and countryside.

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