A journey through Siena and its surroundings
dintorni di siena

Discovering medieval itineraries and great food in the Sienese hills


“Imagine where you want to be, because you will be! Close ranks. Follow me!” Anyone who has heard this phrase already has the landscape and probably the music in mind. The languid Elysian fields evoked by Russell Crowe in the colossal “The Gladiator” are none other than the beautiful Sienese hills of the Val d’Orcia, between Pienza and San Quirico d’Orcia.

Cypress trees trace the road between the undulating curves of the land. The gaze is lost among the green vineyards and olive groves. The hand of man does not affect the harmony of the land, integrating abbeys, medieval villages, fortresses and castles into it. In this marvellous territory, no less than four historic centres are UNESCO World Heritage Sites, including San Gimignano, Pienza and the Val d’Orcia, as well as the historic centre of Siena.

Those who undertake a trip to Siena and its surroundings expect countless facets of culture: the stories told by the monuments, the square in Siena beaten by the horses during the Palio, the way of life and the “ganza” personality of the people. And then good food and wine, such as the Vino Nobile di Montepulciano, the pecorino cheese of Pienza, the extra virgin olive oil or the Vernaccia of San Gimignano.

Whether it is a day trip, a weekend or a longer holiday, the mild seasons are ideal for exploring the most beautiful villages around Siena such as Montepulciano, Montalcino or San Galgano.

The itinerary proposed here will take you from the historic centre of Siena to the nearby villages, crossing the territory in all its beauty!


🧳 Explore Siena and its surroundings with gusto!


What to see in the City of Italy’s most famous Palio

siena italy
Pixabay, bearinthenorth


Like many cities in central Italy, Siena grew out of an Etruscan settlement that was later Romanised, and in the Middle Ages developed from the road. But why the road? Once trodden by pilgrims and merchants, Siena still connects to Rome and more distant France. An old track of the Via Francigena within the city bears witness to the ancient crossroads it represented, in a medieval world where motorways were not contemplated.

Surrounded by walls that define its boundaries, it allows access to the historical centre from numerous gateways, including Porta Camollia, closer to the historic University of Siena, or Porta Tufi, which provides quicker access to the heart of the city (there is also a convenient car park nearby).

Strolling through the alleys of Siena, without realising it you will pass from one “contrada” to another. There are no less than 17 of them and they divide both the city and its citizens! Note that it is precisely these districts that create the bond between human beings and the territory that flows into the vortex around which the life of the citizens of Siena revolves: Piazza del Campo, the famous paving stone of the celebrated Palio di Siena!


Pixabay, gate74


Before starting the city tour, it is mandatory to recharge your batteries at the historic Pasticceria Nannini, where you can enjoy typical sweets such as ricciarelli, panforte, panpepato or cantucci.

Once you have had your fill, you will realise that numerous palaces encircle the borders of the square: Palazzo Chigi Zondadari, the Loggia della Mercanzia, the Palazzo del Comune inside of which is the “best manifesto of the common good” made by Simone Martini and Ambrogio Lorenzetti.

At 88 metres high, the Torre del Mangia towers over the square. Did you know that it inherits the epithet of one of the first bell-ringers, accustomed to “eating food and… money”?


cattedral of siena
Pixabay, Anajim


A stone’s throw from the square is the magnificent Duomo di Siena, whose aesthetics absorb French Gothic and Pisan styles: the black and white marble on the immense columns is truly unique!
Then, there is the Piccolomini Library where the cycle of frescoes by Pinturicchio lies: a must-see to which we can add a visit to the adjacent museum complex of Santa Maria della Scala.

Another crucial square for the development of the city was Piazza Salimbeni, around which the financial activities of one of Italy’s oldest banks, Monte Paschi di Siena, took place. Continuing on foot, you can reach from there the house of Saint Catherine, patron saint of Italy, incorporated within a sanctuary, and finally the Medici Fortress, the ideal place to enjoy a few moments of tranquillity away from the crowded city centre.

There is no shortage of churches in many different styles. The Romanesque Basilica of San Clemente in Santa Maria dei Servi is a place to go at sunset, as it is one of the city’s vantage points, just a stone’s throw from Porta Romana. The Basilica di San Francesco has got an atmospheric interior with large Gothic windows that filter the sun’s rays through coloured glass!

In short, Siena is a concentration of architectural and cultural beauty… But beyond the walls, what awaits you? 😉


Wonders around Siena



Perched on a hill, Monteriggioni amazes with its walls that will immediately take you back to the 13th century! The main gateway to this delightful walled city is Porta Romea. From the Porta di Ponente, on the other hand, you can look towards Florence. The Castle of Monteriggioni dominates the defensive scenario: inside you can walk along the wall walkways that emulate the ancient patrol routes. From here the panorama stretches over the Chianti hills and the distant towers of San Gimignano can be glimpsed.

In the tiny historic centre, there is everything you would expect from a medieval village: stone houses, narrow streets, Romanesque-style churches such as the Church of Santa Maria Assunta and the Abbey of Saints Salvatore and Cirino. Not to be missed is a visit to the Armour Museum, where you can retrace the history of weapons, helmets, swords and wear armour in full Assassin’s Creed style (a video game that chose this very village as its setting). And if you are travelling along the Via Francigena, the stop is a must!



colle val d'elsa
Pixabay, DanielWanke


It is a small medieval town between Siena and Florence that specialises in the art of crystal working. Consider that most Italian crystal is produced right here! The history of this manufacturing is told at the Crystal Museum located on Colle Bassa. On the other hand, on Colle Alta, there is the Castle and the village, the central hub of the town. It is interesting to know that one of the nails of the Crucifixion is kept inside the Cathedral, also known as the Co-Cathedral of Saints Albert and Martial. In the immediate vicinity, outside the walls, natural thermal baths known as “caldane” offer the possibility of immersing oneself in nature while drawing numerous benefits for the skin.



With its 14 towers dominating the hilly landscape of Siena (at one time there were as many as 72), San Gimignano boasts a UNESCO World Heritage-listed historical centre. At the foot of the Devil’s Tower, at the highest point of the town, Piazza della Cisterna, with its octagonal well in the centre, serves as the centre of trade. Further down, Piazza Duomo is surrounded by historical buildings such as the Palazzo Pubblico flanked by the Torre Grossa (54 metres high) and the Palazzo Comunale.

Not far from there, the Collegiata di Santa Maria Assunta houses works by Jacopo della Quercia while the Cappella di Santa Fina contains a cycle of frescoes by Domenico Ghirlandaio dating back to 1475. For the “stronger”, the Torture Museum (there is also one in Siena or Montepulciano) is an attraction not to be missed! For a spectacular view, go to the Rocca di Montestaffoli, from where you can admire the Vernaccia vineyards typical of the area from above and the Wine Museum will allow you to discover its secrets!



tuscan towns


It is a town that has nurtured the culture of Nobile wine-making over the centuries, making this practice a hallmark of the city (so much so that the entrance gate is called the Gate of Bacchus!) Walking uphill through the historic centre, you arrive at Piazza Grande, home to the triad “well-city hall-cathedral” and a meeting point where events and happenings take place. Just outside the walls, the Church of San Biagio is a very special temple of Renaissance architecture that reaches towards the sky, totally surrounded by greenery.



The Renaissance village par excellence, the dream of the humanist Aeneas Silvio Piccolomini (later Pope Pius II), is located in the beautiful setting of the Val d’Orcia. As for many of the picturesque villages mentioned here, crucial elements are enclosed around the main square: the well, the source of life, which here takes the name “Pozzo dei cani” (Dog’s Well); the Duomo or Cathedral of the Assumption, with its octagonal bell tower that marks time; and finally the administrative palace, in this case Palazzo Piccolomini, from where you can access the Loggia with a marvellous view over the surrounding panorama. And, if you continue in the direction of Pieve di Corsignano, a walk will take you to the church where Pope Pius II and Pope Pius III were baptised. Don’t forget to enjoy a typical lunch and buy a gastronomic souvenir (being careful not to eat it in the street). The good local cuisine offers the typical Pecorino di Pienza, a cheese that goes well with anything, especially with pici!



It encapsulates the essence of the entire Sienese territory. The delightful medieval village is located in the Val d’Orcia and, besides being a sinuous example of medieval architecture, Romanesque-style churches such as the Church of Santa Maria Assunta or the Collegiate Church of San Quirico and Giulitta, it gives us that mental representation you have of Tuscany. Do you remember the Elysian fields I mentioned at the beginning? The roads flanked by lonely cypress trees, the fields of wheat and the remote and fascinating churches like the Chapel of the Madonna di Vitaleta. Everything here is in harmony with nature and the thermal baths of Bagno Vignoni are an emblematic example. Impossible not to dedicate a day to these enchanted places.



Whether for a day trip or crossing the paths of the Via Francigena, it is well worth visiting this village despite the fact that there are barely a thousand souls, tied to ancient traditions and religious rites (especially those of Holy Week). The architecture that makes this town attractive is undoubtedly the Rocca di Radicofani, a fortress that today houses the Cassero Museum. It is also interesting to enter the town park, called Bosco Isabella. It was built by the Luchini family and contains specimens of plants from different parts of the world.



italy siena
Pixabay, misterfarmer


South-west of Siena lies one of the most incredible places of medieval representation. It is the Abbey of San Galgano. With its French Gothic style, it is able to envelop you in the mystery and fascination of its walls stretching out towards the open sky, without a roof! The moon passing through the rose window completes the picture of this striking open-air abbey. The framework of the ceiling was sold around 1500 on Leopoldine pressures and, in the late 18th century, it was removed entirely. In the nearby Hermitage of San Galgano in Montesiepi, a sword in the rock is the protagonist of a myth far removed from the magical excalibur. Galgàno Guidotti, an armed knight, abandons his sword to live as a hermit. It is the story of a sword that becomes a cross, of a knight who becomes a saint.



These are among the most beautiful natural thermal springs in central Italy and are located between the provinces of Siena and Grosseto. In an enviable natural context, between the Val di Merse and the Farma River, these calcareous waters were known even to the Etruscans and, in time, were the destination of popes and lords such as the Gonzaga of Mantua. Their beauty goes beyond the natural context as the hand of man has created defensive walls around them, making them true fortified spas. It is absolutely worth taking a relaxing break in this paradise.



Listed among the most beautiful villages in Italy, San Casciano dei Bagni is a perfect destination to integrate a sightseeing tour inside the village and a few hours of absolute relaxation at the thermal baths. As can be deduced from its name and the town’s coat of arms (which depicts three naked women inside the baths), San Casciano is known for its thermal baths immersed in the peaceful hills at the foot of the town. It follows a circular route that passes by the Insigne Collegiate Church of San Leonardo and the adjacent Church of Sant’Antonio, for centuries the active centre of the town’s religious and community life. Finally, we arrive at the highest point where the Castle of Fighine stands. Despite being a very small village, San Casciano dei Bagni, like Siena, is divided into four contrade (districts) that challenge each other in a goliardic Palio della Ranocchia!



Unsplash, Luca Micheli


There is nothing lacking in the Italian territory, not even “lunar” landscapes. Near Siena, there are grey-blue clay expanses stretching for kilometres and kilometres south of the province of Siena, between Asciano, Buonconvento, Montalcino, San Giovanni d’Asso, Monteroni d’Arbia and Trequanda.

Starting from Monteroni d’Arbia, you can make an initial pit stop at the 14th-century Water Mill. In Buonconvento the agricultural culture is deeply rooted and deserves a closer look at the Museo della Mezzadria.

An important stop in the Crete Senesi is Montalcino. This amazing town is known to most for the goodness of Brunello di Montalcino, a wine that pairs naturally with the white truffle of nearby San Giovanni d’Asso. Here, the flavours of this white treasure delight visitors to the Truffle Museum, inside the magnificent castle.

The main centre of the Crete Senesi is undoubtedly Asciano. This medieval village is so rich in history that it is deeply linked to religious craftsmanship that there is a Museum of Sacred Art inside Palazzo Corboli. From a morphological point of view, the most characteristic part of the Crete Senesi is the Accona Desert, a semi-arid area near Asciano, where the terrain is characterised by particular formations such as “biancane”, “calanchiandbalze”.

Between Asciano and Buonconvento, a small diversions will lead you to the Abbey of Monte Oliveto Maggiore, a fascinating place of worship where the loneliness of the walls is softened by the breathtaking landscape.



visit siena
Flickr, Daniele Porro


Near Siena, not far from Montalcino, you will find the Abbey of Sant’Antimo. It is a place whose history dates back to 352, the year of the death of Saint Antimo of Arezzo. From a small oratory to a refuge for monastic communities such as the Premonstratensians or the Olivetan Benedictines. Inside, mighty columns surround the high altar and crucifix, creating a mystical atmosphere. In the crypt lies the Saint’s tomb. A visit to this wonderful time portal is definitely worthwhile!



siena in italy
Flickr, FRANCO600D


The province of Siena embraces a particular hilly territory, in the common language called “Chianti Senese”. It includes the municipalities of Radda in Chianti, Gaiole in Chianti, Castellina in Chianti, and Castelnuovo Berardenga.

Here you can also move around following your instinct, letting yourself be carried away by the beauty of the hills, following the tops of the towers, stopping to visit castles and abbeys, but above all letting yourself be carried away by the scents of the rows of vines. The vocation of the territory is undoubtedly wine and relies on the protection of the Chianti Colli Senesi Consortium. Chianti wine is characterised by the most widely used grape variety: the typical Tuscan Sangiovese. It is worth choosing a food and wine itinerary to savour the Chianti hills of Siena in all their purity!

As you can see, the surroundings of Siena are as picturesque as they are rich in activities


Here are some things to do near Siena:

1. Explore the Crete Senesi by steam train: dedicating a day to this itinerary is a truly distinctive experience. The Trenonatura project provides this service using the old Asciano – Monte Astico railway line. The train stops at the various villages in the Val d’Orcia, also allowing longer stops for nature walks.

2. Doing outdoor sports such as biking, trekking or hiking in nature. The Colle-Poggibonsi cycling track is among the most interesting routes. There are numerous reserves, including the Pietraporciana Nature Reserve, the Basso Merse Nature Reserve or the Sentierelsa trails that wind their way from the waters of the Elsa River and lead to the Alta Val d’Elsa River Park. A comfortable setting is the forest, especially if adorned with sculptures or attractions that will make even the youngest children happy, such as the Chianti Sculpture Park just 10 kilometres from Siena or the Bosco della Ragnaia.

3. Stroll through the Elysian Fields of Val d’Orcia, totally immersing yourself in nature. If you like the idea, you could consider doing it not necessarily on foot but on horseback or on a Vespa! The electric bike could also be a green alternative, giving you time to visit other places.

4. Relaxing moments at the thermal baths: you are spoilt for choice between Bagni San Filippo, Bagno Vignoni, Rapolano Terme, San Casciano dei Bagni or Terme di Petriolo. The thermal waters of the Sienese territory are a panacea for the body but also for the mind, and the ancient Etruscans and Romans certainly thought the same. The naturalistic setting where they are set is enviable, so if you are in the area, you cannot miss them!

5. Taste the local food & wine and join food and wine activities such as tastings, cooking classes, dinner in the vineyard, picnics, dinners in the olive grove. Special dedication should be given to the white truffle, which you can find during truffle hunting tours. The scents of the forest are reflected in the dishes, and strong flavours are the hallmark of Sienese cuisine, which abounds in Pecorino di Pienza, game meats, Chianina meat and sauces that complement first courses such as Pici!

Of course, the value of Tuscan extra virgin olive oil and saffron from San Gimignano is unquestionable. Together with the great wines of the area, they create the outpost of Sienese gastronomy.

You are bound to taste (unless you are a teetotaler) Brunello di Montalcino, Chianti Colli Senesi, Vino Nobile di Montepulciano, Vernaccia di San Gimignano and Orcia DOC, following the tasting itineraries of the Wine Routes.

6. Follow the Via Francigena trail on a spiritual itinerary that will connect you with nature. The signs on the route will take you to unexpected villages and beautiful people!

7. Rediscover isolated abbeys and castles such as the Abbeys of San Galgano, Sant’Antimo or Monte Oliveto Maggiore. Among the castles, Belcaro Castle, Celsa Castle or the wonderful Brolio Castle.

8. Don’t miss a visit to the local museums! Everyone’s taste is catered for, from History and Archaeology Museums to those dedicated to the Middle Ages such as the Torture Museums or the one dedicated to the Knights Templar in Monteriggioni. There are Museums of Weapons, of Sacred Art, of Crystals or of Terracotta (in Petroio), but also those dedicated to food and wine such as the Brunello di Montalcino or the Vernaccia di San Gimignano Museums.


Events in Siena and its surroundings

Pixabay, Palmik


A very brief mention of some traditional events, including of course the Palio di Siena, which takes place twice a year, completely transforming Piazza del Campo into a wild arena.

In Monteriggioni, usually in July, six days of festivities are dedicated to medieval customs, so much so that a traditional medieval banquet full of Tuscan delicacies is recreated!

The month of September is for cheese lovers: in Pienza, the “Fiera del Cacio Fuso” is entirely dedicated to pecorino cheese, but there is also room for other traditional foods. Within the fair, a real Palio del Cacio (cheese competition) pits the districts against each other. They must rotate a wheel of pecorino cheese around a wooden spindle placed in the centre of the square!

All you have left to do is set your diary and plan an escape among the wonders of Siena and its surroundings… Enjoy your trip to Tuscany!😉

About Author

Emmanuela Governali
Sicilianissima amante del cibo da 29 anni e laureanda in Scienze e Cultura della Gastronomia a Padova. Vivo in provincia di Palermo e scrivo cercando di comunicare il valore emozionale di ciò che ruota attorno alla tavola. Storia e tradizione sono la chiave per interpretare luoghi, pietanze e persone e io amo catturarne i dettagli con parole e scatti: ad ispirarmi sono i ricordi della cucina di famiglia.


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