Monteriggioni: what to see in the town nestled in the Tuscan hills
monteriggioni cosa vedere

Monteriggioni is a top Tuscan destination! Here you can find the complete guide to visit Monteriggioni castle and its surroundings among art, nature, food and relax.


Monteriggioni is a small town in the province of Siena, in the heart of Tuscany, part of the Montagnola Senese.

This is one of the most famous hilly areas in Italy with a dense presence of woods and a soil rich in marble, which in the past was widely exploited for trade and was used to build Florence Cathedral. One of the particular characteristics of the area is the large number of caves.


monteriggioni castle
Flickr, Ignacio Ferre Pérez


Here, time seems to stand still, it looks like a picture-postcard place, almost like a fairy tale with its small houses and narrow streets with towers and a castle. In the evening, the lights illuminate it entirely, forming a sort of mirage among the Tuscan hills. The town is famous above all for its history, monuments and the possibility of moving freely between landscapes and nature.


Does this village fascinate you? Discover it with an 8-day trip through villages and taste!


Monteriggioni Castle

During the Middle Ages, the castle was built by the Sienese by order of Guelfo da Porcari. It then became the site of an ancient Lombard farm. The Republic of Siena used it as a defensive point.

The town is located on Mount Ala and offers a privileged position for admiring the surrounding landscape and watching over the Via Francigena. It was once used to control the Elsa and Staggia valleys as far as Florence.

The castle was built following the natural inclination of the hill. It had been the object of clashes between the Florentines and Sienese for a long time. Between 1400 and 1500 the town became the seat of the artillerymen, but the battles for the Castle continued. Today it belongs to the Griccioli family who own the Castle and all the surrounding countryside.


walled city in tuscany
Flickr, Marco Marano


From a landscape point of view, Monteriggioni Castle seems to dominate the whole town, which in itself is small and fortified. Today it is one of the most famous Italian walled cities, even mentioned by the Italian poet Dante Alighieri.

Visiting Monteriggioni means being enchanted by its slowness. There is no frenetic life here, the economy is based on agriculture and breeding, there is a lot of craftsmanship and excellent cultural integration. The perfect place for those who love culture and history, who want to relax while admiring the Tuscan hills and enjoy the spectacular local food and wine.


The Via Francigena

The Via Francigena, which linked Northern Europe to Rome, once passed through here. The great testimonies that are still visible today are the Abbadia a Isola, the Pieve di Santa Maria a Castello and, in Monteriggioni, the Pieve di Ponte allo Spino in Sovicille.

At the time, the Via Francigena, also known as Via Romea, was a set of routes that became famous as a destination for pilgrims and crusaders embarking for the Holy Land. In the Middle Ages, pilgrimages to Rome, especially to the tomb of Peter the Apostle, took place continuously from all over Europe. Many stopped in Rome, while others continued throughout Italy as far as Apulia.

Tuscany was a favourite stopping place, in particular the province of Siena. The Via Francigena was first attested in 1204, while it was not until the 10th century that it was first described. Since 1994, it has become one of the most famous cultural routes in Europe, compared to the Camino de Santiago de Compostela.


monteriggioni italy
Flickr, Raffer


In the specific case of this amazing town, the stop was Pieve di San Giovanni Battista, a sacred building located in Ponte allo Spino and representing the archdiocese of Siena-Colle. The exact date of its construction is not known, but the first traces date back to 1189. Today it is one of the most important Romanesque buildings in Italy with three naves. Inside is a panel painting by Bartolomeo Neroni depicting the Madonna and Child.

Monteriggioni is not only famous for being one of the stops on this pilgrimage, but also because it is a town as small as it is magical.

Follow me in the reading and we will discover better what to see in and around the town. 😉


The best things to do in Monteriggioni

Despite its small size, it has plenty to offer visitors. It is very easy to get around and even a day is enough to visit the entire town. The station that serves the area is on the Empoli-Siena line. It is located in Castellina Scalo, which is about 4 km from the town but easily accessible.

For a complete itinerary, we will explore all the unmissable places in town. 


What to see in Monteriggioni

1. City walls

The main attraction is the Cinta Muraria (City Walls), one of the most beautiful and characteristic examples of military architecture in the world. It extends 570 metres and was built between 1212 and 1219, then reinforced in 1270. It served to protect the territory from Florentine attacks. The city walls were so famous that they were mentioned by poet Dante Alighieri in his “Inferno”, where they are depicted with a simile of the Giants, referring to the city towers.

The city walls seem to literally embrace the whole town. The towers and perimeter are imposing and can be admired from far away. Along the route you can admire 14 towers that exceed 20 metres in height.

They all have a square base and are in good condition: only one of them is half-finished and therefore only a stump. Here you can walk along the city walls. Only since the 2000s have they been opened up and there are two different routes: on both sides you can admire the view.


monteriggioni tuscany
Flickr, Raffer


The walkways are partly accessible for a fee. Tower 1 can be visited but there is a charge for access from the South walkway. The northern walkway begins between towers 7 and 8 at the Porta Fiorentina. To continue in this case you have to pay another ticket.

From tower number 9 onwards, it is not possible to continue because the sections are private or not accessible. Tower 13 has a walled door that once served as access to the walled city. Walking along the walls it is possible to admire spectacular views over the Montagnola Senese and Chianti.

The land at the foot of Monteriggioni was once a swamp, but thanks to the work of the monks it has been reclaimed with a water tunnel. In the centre of what was once a swamp, it is now possible to admire the “Torre della Bonifica” with its underground tunnel (which cannot be used today because it is occupied by debris).


2. The Gates

Among the best things to see in Monteriggioni, a visit to Porta Franca, also known as Porta Romea, which is the entrance to the town, is not to be missed. It faces Rome and consists of a large tower with a pointed arch. There was probably once a drawbridge here, but there is no trace of it today. On the left you can admire the inscription of the foundation of the town.

On the opposite side stands the Porta di Ponente, which faces Florence and has Dante’s verses inscribed on it. The Porta Murata (Walled Gate) is no longer accessible today, but together with the other two gates it formed the entrance to the walled city.


tuscan countryside


3. Piazzale Roma and Museums

The heart of the town is Piazza Roma: from this point, the entire urban nucleus develops. The town has not many squares and this is the “piazzetta” for everyone. Until the 1970s the square was not even paved, it was then paved using the Rosia quarries which are still in perfect condition today.

The medieval city gates lead into this square. Here you will find the town’s Tourist Office, the Arms Museum and the Church of Santa Maria Assunta. There are many bars and inns where you can take a break and this is also the point for all the events and happenings in the town.

The Museo di Monteriggioni In Arme is the main one in the town. Here all the historical monuments of the walled city are displayed with many models explaining the siege techniques, the battles and the means used. Some weapons are not only visible but can even be handled. An incredible cultural experience to visit this Tuscan town and discover everything about the ancient local traditions.


tuscany village
Unsplash, Shalev Cohen


Abbadia Isola, where the former abbey of Santi Salvatore e Cirino stands, and the hermitage of San Leonardo al Lago, which we will discuss later, also deserve attention.


What to do in Monteriggioni


1. Sport and Nature

It is worth taking a stroll around the entire urban perimeter with a stop at the Towers and City Walls. The local museum and the tourist office organise pleasant cultural walks to discover the history of the town.

For those who love sport and outdoor activities, it is possible to go hiking on the nearby hills and organise mountain bike excursions to admire the breathtaking views from above.


2. Food and wine

Food and wine lovers can also enjoy food and wine-themed itineraries and tours, picnics in the open air and local delicacies. You absolutely must try Agro e dolce, a dish made with sugar and lemon, pork steak with turnips, tripe thistles, stuffed onions, wild boar offal, Maremma pancrocino, fried pasta, pici with briciolata sauce, Mugello-style tomatoes, sausages and cabbage soup.

There are also plenty of farms and wineries in the area where you can enjoy all kinds of food and wine tastings. Being in the heart of Tuscany, it is impossible not to savour the incredible wine produced here. Among the local wineries there is Casa Vinicola Bartali, which produces incredible Brunello, Chianti, Vernaccia and Vecchia Corona wines.


3. Hermitages and sacred places

Nearby you can discover the Hermitage of San Leonardo al lago, a building located near Santa Colomba. This Augustinian hermitage was first documented in 1119, and there are many frescoes inside that make it so characteristic.

The Pieve di Santa Maria a Castello is one of the most interesting symbols of Siena, an important testimony to the history and disputes concerning the exchange of property with the Catholic Church. The church was restored in the 19th century when the local population increased, then it was gradually abandoned. Today it can be visited as part of an agritourism. It has been totally modernised, but the baptistery of St John the Baptist is very interesting.

The Abbey of Saints Salvatore and Cirino is very famous in the area. It is located in Abbadia a Isola and was important because the organisations of all the other churches depended on it. Being on the Via Francigena, it was a special place for pilgrims. It is located in the centre of the fortified complex of Abbadia and is a basilica with three naves. Inside there are many works, the fresco of the Madonna, the baptismal font, the Assumption of the Virgin. Many works of art have been brought in later, forming a sort of sacred museum, while others date back to its construction.


When to visit this walled tuscan city

The ideal time to visit the town is between spring and summer for those who love hiking and therefore want to enjoy the temperate climate. Autumn is also very characteristic because, being immersed in the woods, it is possible to admire how nature and its colours change.


Visiting Monteriggioni and its surroundings

The town is also an excellent starting point for visiting nearby towns and villages, starting right from Siena. In the Tuscan town you can admire the medieval buildings, the fan-shaped square and the contrade, one of the unique representations of the territory.

Montepulciano is also worth a visit, for its great wine-making tradition. You can enjoy wine tastings in the world’s best wineries or relax in one of the natural spas.




Montalcino is a very characteristic neighbouring town, small in size but interesting for the production of Brunello wine and its history. San Gimignano is also perfect for wine lovers. Declared a UNESCO World Heritage Site for its historic centre, which is a real gem, it is one of the best examples of urban organisation in Europe.


san gimignano
San Gimignano


Also worth a visit is San Miniato, which lies between Florence and Pisa. It is the area’s most famous industrial centre for leather production, also well known for its white truffles and wine production. Nearby you can also visit Arezzo with its immense cathedral and Seggiano, a little gem in the province of Grosseto.




From Monteriggioni it is also possible to visit Florence, which with its history and culture is one of the most beautiful cities in the world. A walk in the Florentine hills around Certaldo and Pelago is also worthwhile for those who want to admire incredible views.


In the area you can also spend a few hours relaxing at one of the spas. Among the most beautiful and closest are those of Rapolano in San Giovanni. These rise in the heart of the town and are completely natural, with spring waters and hot pools that are literally surrounded by greenery.


Events in Monteriggioni

Despite its small size, this Tuscan town offers a wide range of events to take part in, from festivals to organised tours to discover the walled city. The most important event of all is the Medieval Festival, which is held every year and has never been interrupted since its creation. It lasts about a week in July and encompasses history, culture, food and wine, attracting tourists from all over Europe.

The Medieval Festival was created with the intention of enhancing the heritage of the town, but also to showcase food specialities, artisan crafts, works and popular traditions. For this reason it involves everyone. It opens with a large banquet, there are markets along the streets of the town and a full programme of events with dancing, plays, music and tastings. The beating heart of the whole activity is Monteriggioni Castle, where the citizens participate with the costumes of the period, in an incredible parade of colours and representations.


Flickr, Daniele Redamante


Taking part in the event is a unique way to visit Monteriggioni and take part in the life of the town with its characteristics and its centuries-old history. You are immersed in the local culture, welcomed by the locals who are very happy to meet visitors and show them its great heritage.

Now that you know what to see in Monteriggioni, check out all the food and wine experiences in Tuscany selected by Italia Delight! 😍


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