On the slopes of the picture prefect hills of ‘Val d’Orcia’ lies the medieval town of Montalcino in Tuscany. Today the town is most famous for its ‘Brunello di Montalcino’ wines from world class viticulture and wineries set in a stunningly beautiful environment. The best of all worlds!

As with many other Tuscan hamlets and towns, Montalcino is of Etruscan origin. The first historical documentation of the existence of Montalcino dates from 814 and it was only in the Tenth Century Montalcino slowly grew in size and became more inhabited.

Montalcino map
Montalcino abbey

Being located along the ‘via Francigena’, a pilgrim route from France to Rome, in medieval times was beneficial to the independence and economical advantage of Montalcino, all those thirsty pilgrims! Another important industry in Montalcino at that time was the curing of animal hides and vellum production and the town had many tanneries.

During the Middle Ages and onwards, Montalcino was touched by the conflicts between Florence and Siena, between the Ghibellines and Guelphs. When the Republic of Siena was defeated many noble families from Siena took refuge in Montalcino. So much so, it went under the name ‘Repubblica di Siena riparata in Montalcino’, - ‘The Republic of Siena taking cover in Montalcino’. In the 16th Century, Montalcino, just like Montepulciano, became part of the ‘Grand Duchy of Tuscany’ in which it remained until the Unification of Italy in 1861.


Starting in the main town square, the ‘Piazza del Popolo’ take a closer look at the ‘Palazzo Comunale’ the town hall, with its high bell tower dating to the early 14th Century. Another building of interest close by is ‘La Loggia’ in the Renaissance style and also the ‘Teatro degli Astrusi’ from the 18th Century.

‘La Fortezza’ - the fortress, ‘La Rocca di Montalcino’, was built on the highest point of Montalcino in the 14th Century by Mino Foresi and Domenico di Feo, two architects from Siena. The fortress, pentagonal in shape and incorporating some earlier structures, an ancient cathedral and an old fortified tower was further developed during the Medici era. Today the Fortress houses an ‘enoteca’ where you can find many of the local Brunello wines!


Continuing our tour of Montalcino, there are many churches to admire such as ‘Il Duomo’ or rather ‘La Cattedrale del Santissimo Salvatore’. A cathedral in neoclassical style that is home to some masterpiece paintings such as the 16th Century ‘l’Immaculata concezione del Gesú e Dio Padre’ - the Immaculate Conception of Jesus and Father of God by Francesco Vanni and the 17th Century painting ‘La Madonna Assunta tra angeli con i Santi Ippolito vescovo e Cipriano martire’ – the Madonna Assunta in the midst of the angels with Saint Ippolito bishop and Cipriano martyr by Francesco Nasini.

Don’t miss for the world the majestic ‘Abbazia di Sant’ Antimo’ - the Abbey of Saint Antimo, that is situated just outside Montalcino in the valley below Castelnuovo dell’Abate. The Abbey built in the Romanesque style, is a beautiful point of tranquility, mindfulness and serenity where you feel you have been transported to another time and place upon stepping across the threshold. Ask us at Tuscany Destinations for more information about how to set up a complete guided tour of the local churches.

madonna montalcino
museum Montalcino


For those who are very fond of art, don’t forget to pay a visit to the ‘Museo Civico e Diocesano d'Arte Sacra di Montalcino’ – the Civic and Diocesan Museum of Sacred Art of Montalcino that is located in the former Sant’ Agostino Convent. Here, take a journey in local art from the Middle Ages up until the 20th Century covering many well-known painters such as Bartolo di Fredi, Simone Martini, and Ambrogio Lorenzetti.

What would Montalcino be without a museum focused solely on the production of ‘Brunello di Montalcino’ wines? Not far from the road that leads to the ‘Abbazia di Sant’ Antimo’ you can find the ‘Museo della Comunità di Montalcino e del Brunello’ and learn more about this unique grape variety and the so very delicious, sought-after wines.

montalcino restaurant
montalcino restaurant 2

Caffé, Bar, Restaurant

Where to Eat and Drink

We are now touching upon a topic where we could talk for days and days about food and wine in Montalcino. At Tuscany Destinations we can most assuredly help you find something for your taste buds on your dream vacation in Tuscany.

To mention a few; ‘Trattoria Il Pozzo’ just outside Montalcino serves traditional Tuscan food made from local produce. Perhaps a combination of wine bar and restaurant is what you are looking for? Then ‘Il Leccio’ is the place for you. A stylishly modern wine bar that also serves food in the centre of Montalcino is ‘Drogheria Franci’. Would you like to have lunch or dine at a winery? Then why not try ‘Ristorante di Poggio Antico’.

And the wine then?

A visit to at least one winery is a must when you find yourself in Montalcino in Tuscany on your dream vacation.

There are around two hundred wineries producing ‘Brunello di Montalcino’ wines, so it is a little difficult to give a brief overview of them. We recommend visiting a mix of better known wineries, as well as the smaller gems known only to the locals or those ‘in the know’. There are also different styles of winemaking, the use of barriques to mature the wine in which caters to a more international taste and a focus on big casks for a smoother and more elegant Brunello wine.

At Tuscany Destinations we are happy to organize the best wine tours for you in Montalcino.