Unforgettable Holidays in and around a medieval hilltop village in Southern Tuscany
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About Montisi

About Montisi

Montisi is a beautiful medieval hilltop village in Southern Tuscany just half an hour south east of the magnificent city of Siena and about 2 hours drive north of Rome. Very close to the famous wine towns of Montalcino, the home of Brunello, and Montepulciano, the home of Vino Nobile, Montisi is home to some 400 people and is full of character and many surprises for so small a village.



It is likely that the village of Montisi was home to the ancient Etruscans and the earliest reliable documents date back to the 12th Century when Montisi was a castle belonging to the Counts of the Scialenga, part of the Cacciaconte family. In 1291, the three Cacciaconte brothers, Simone, Fazio and Cacciaconte claimed the revenues from the village, something which the Montisani probably didn’t accept and the following year, Simone Cacciaconte attacked the village and conquered the castle. Realising he wouldn’t be able to hold it without support, he burned the village down. The Commune of Siena banished the Cacciaconte and this event is remembered each year in August at the festival of the Giostra di Simone.
giostra band (940x331)

Montisi today

Today, Montisi is a thriving community with several places to stay and a number of restaurants. It is home to a number of artists and artisans as well as a world famous harpsichord school, a cinema and a theatre. The village is divided into four districts, San Martino, Piazza, Castello and Torre, known as ‘Contradas’ and there is healthy competition between them especially during the Giostra di Simone which is held in August every year! During the year each of the districts hosts various events and during festivals the village is adorned with flags waving from all of the houses and the Montisani wearing colourful scarves. I live in the district of San Martino – I think it’s the best – and we always produce the most delicious food when it’s festival time. Montisi is also well known for some of the best olive oil Italy has to offer and every October celebrates with an Olive Oil festival, which attracts visitors from all over Italy.


The Giostra di Simone

This very important festival remembers the actions of Simone Cacciaconte and takes place on the Sunday closest to the 5th August each year, which is the feast day of Montisi’s patron, Our Lady of the Snows. The festival lasts several days and there are a host of dinners, processions and special events including a flag waving competition. The festival culminates in a competition on the Sunday when four knights, one representing each of the four districts – San Martino, Piazza, Castello and Torre – compete in a tournament by attempting to strike a target known as a ‘burrito’ with their lances at a full gallop. The burrito is an effigy of the wicked Simone Cacciaconte and the knight must try to put his lance through a tiny ring on the shoulder of the burrito. It’s incredibly difficult, the more so because of the deafening cheers of the watching crowd.

The competition itself is preceded by a very solemn but wonderfully colourful medieval procession through the streets of the village and in 2013, I was honoured to be the Dame for the Contrada of San Martino. Imagine spending an afternoon in 40 degrees dressed in a velvet gown and knee high leather boots. It was an incredible experience and one that I shall never forget.

Olive oil festival - band

The Olive Oil Festival

This festival takes place at the end of October each year and the village streets are festooned with flags and lined with stalls displaying the newly pressed olive oil for which the area is famous and selling meats, cheeses, wines and local crafts. With events each evening celebrating the olive harvest and a brass band marching down the streets it’s a really fun weekend and one which attracts visitors from all over Italy as well as many tourists. If you like the idea of wandering up and down the pretty medieval streets, tasting olive oils and sampling all the delicacies this area has to offer, then you must come and visit.


We now have a new village website which I have set up for the benefit of the village www.montisi-montalcino.com. Please do visit our new site for the latest info in and around Montisi.