Pienza and surroundings: what to see near Pienza?
dintorni di pienza

What to do in and around Pienza? If you have never visited this small town in Tuscany, find out what to see in the area around Pienza, including nature, history, art, food and wine.


Pienza is a small village in Tuscany, in the province of Siena, in the fantastic setting of the Val d’Orcia. This area is characterised by wonderful hills, vineyards and olive groves. In addition to offering excellent food and wine, including pecorino di Pienza and Brunello di Montalcino, this corner of Tuscany is able to offer breathtaking landscapes, almost surreal, so much so that it has been included in the UNESCO World Heritage Sites.

The origins of this town can be traced back to Enea Silvio Piccolomini, later Pope Pius II, who decided to transform his birthplace, Corsignano, into the ideal city of the Renaissance. Pienza thus becomes a fascinating town where fantastic architecture is combined with beautiful natural surroundings. The landscape is truly enchanting, without forgetting the neighbouring villages of which we will speak later.

Are you curious to know everything you can visit near Pienza? Then read on!


Visit this corner of Tuscany! See all experiences and travel ideas


What to see in and around Pienza

In this article, I am going to introduce you to this beautiful town with all its characteristics, without forgetting some of the most beautiful villages in Italy that are located in the surroundings of Pienza.

If you don’t know what to see near Pienza, don’t worry and let yourself be inspired by this reading!👇





As I told you, Pienza is a small town in the province of Siena in Tuscany. Its origins are very recent, compared to the more ancient villages located a few kilometres away from the city.

The town was only founded in the 15th century by Enea Silvio Piccolomini, who later became Pope Pius II. The latter wanted to create an ideal Renaissance town. Thus Corsignano, Piccolomini’s birthplace, was transformed into Renaissance Pienza by the architect Bernardo Gambardelli, a pupil of the more famous Leon Battista Alberti.

The most important buildings to see are the Cathedral of Pienza, in Gothic style with Renaissance overtones, and Palazzo Piccolomini. Opposite the latter is Palazzo Borgia and both overlook the wonderful Piazza Pio II, the town’s meeting place. The Pieve di Corsignano, in Romanesque style and very suggestive, is also worth a visit.


pienza italy
Flickr, Andreas Peters


For nature lovers, I recommend a walk in the greenery of the fantastic village of Monticchiello, a hamlet of Pienza. With a medieval rather than a Renaissance layout, this small village dates back to 1200 and still has the remains of the walls, the castle and the keep. The town’s landmark building is the Church of Saints Leonard and Christopher, which houses important frescoes of the Sienese school. A very nice initiative that takes place in Monticchiello is the Poor Theatre. It consists of putting on a show once a year in the summer on a theme decided by the population. If you are in Pienza and its surroundings, don’t miss this particular event.


pecorino di pienza


The local food and wine include the renowned pecorino di Pienza cheese, pici and Colli dell’Etruria Centrale DOC wine. To conclude, I recommend a typical event in this town, the “cacio al fuso” game held in September.



montalcino italy


Montalcino is a small village in the Val d’Orcia, surrounded by greenery and protected by imposing walls. One of the symbols of this town is undoubtedly the castle: it dominates the entire scenery and from its summit you can enjoy a truly breathtaking view.

Visitors should not miss the main square, known as Piazza del Popolo, and the two churches of Sant’Agostino and Sant’Egidio. For art lovers, the Civic and Diocesan Museum of Sacred Art is very interesting. Almost forgot, don’t miss to visit the Abbey of Sant’Antimo, which is believed to have been founded by Charlemagne!

Among the events, the Jazz&Wine Festival deserves a mention, while as far as food and wine are concerned, you must absolutely try the Cinta Senese cold cuts, to be paired with the sumptuous Brunello di Montalcino DOCG.





What to see in Pienza and surroundings? If you have never been around Pienza Italy, I suggest you visit Montepulciano, a town known throughout the world for its wine production, to which it also gives its name. The town is located on top of a hill and, from some strategic points, you can enjoy breathtaking views over the surrounding vineyards and olive groves. On some days, if you are lucky, you can even see the imposing Gran Sasso d’Abruzzo, a massif in the Apennine Mountains.

The main street of the town is the so-called Corso. From there, you can easily reach the Pulcinella Tower with its typical mask that marks time every hour. The heart of Montepulciano is Piazza Grande, overlooked by the Palazzo Comunale, the Palazzo del Capitano del Popolo and the unfinished Duomo.

Art lovers should visit the Civic Museum and the Crociani Art Gallery, while a visit to the wine cellar, where the famous Nobile di Montepulciano wine is kept, is truly evocative.
Outside the walls, surrounded by greenery, is the wonderful Church of San Biagio, a symbol of Renaissance architecture.

Typical products such as pappardelle with hare sauce and grilled porcini mushrooms are a must, all paired with the famous Vino Nobile di Montepulciano DOCG.


San Quirico d’Orcia

san quirico d'orcia


This is a charming village in Tuscany, in the beautiful green Val d’Orcia, characterised by the presence of cypress trees, vineyards and olive groves that provide truly unforgettable landscapes.

The Collegiate Church with the Church of San Francesco is very important for the town, but the Church of Santa Maria Assunta with its fantastic rose garden is also worth a visit. Among the civil architecture, Palazzo Chigi and the Horti Leonini, a typical Italian garden, are of great importance. Outside the walls, halfway between Pienza and this fantastic town, there is the Cappella della Madonna di Vitaleta, a late Renaissance church surrounded by nature.

I also recommend a visit to a hamlet of San Quirico, Bagno Vignoni. The latter is characterised by a water square fed by a spring with water at 52°C, which in winter gives very evocative effects. If you are a nature and spa lover, this small village is perfect for relaxing and recharging your batteries!

Let’s conclude with the local food and wine offer that includes pici with goose sauce, bread soup, “Terre di Siena” olive oil PDO and the famous saffron. As for wine, don’t miss the Orcia DOC.



Flickr, Ernst Haas


If you don’t know what to visit in Pienza and the surrounding area, then let us recommend this fantastic medieval village. Buonconvento is a small Tuscan village that still retains the relaxed atmosphere of times gone by.

Walking through its alleys, you will see beautiful stone houses, flowered balconies and (of course!) important monuments. One of the most significant buildings in this town is undoubtedly the Palazzo Podestarile with its 14th-century civic tower, but don’t forget the famous Church of Saints Peter and Paul. If you are an art lover, don’t miss the Museum of Sacred Art with works of art by some of Tuscany’s most influential artists such as Duccio di Buoninsegna and Pietro Lorenzetti.

The carnival with its parade of allegorical carts is one of the main events in the village, while as far as local specialities are concerned, try bruschetta, panzanella and cantucci biscuits, paired with a good Val d’Arbiae d’Orcia DOC.



Flickr, Ornella D. (ornedra)


What to see near Pienza? Radicofani is a charming village in the Val d’Orcia near Pienza Tuscany, that is well worth a visit.

Situated in the province of Siena, thanks to its strategic position on the top of a hill, it offers breathtaking views over the whole valley. On clear sunny days, it is possible to see the majestic Mount Amiata, Lake Bolsena and Lake Trasimeno.

With regard to the village, we can say that it has kept its typical medieval structure intact, with its stone houses and narrow streets. The Palazzo Pretorio and Palazzo della Posta are a must-see, while the religious buildings are the Church of San Pietro, in Romanesque style, and the Church of Sant’Agata, in Baroque style. However, the symbol of the town remains the imposing fortress that dominates Radicofani and the entire valley. From its height, it offers unforgettable views.

Let’s conclude by talking about the local food and wine. Definitely worth trying are the sciornini in broth, the omelette with strigoli and the sweet buristo. As for wines, let me recommend the Toscana IGT.


Castiglione d’Orcia

castiglione d'orcia
Flickr, Dino


Castiglione d’Orcia is a small village in the province of Siena, in the Val d’Orcia. The centre of this charming village is represented by the main square known as “Piazza Vecchietta”, where there is a travertine well dating back to the 16th century. The most important monument is the Aldobrandesca fortress, of which all that now remains are the walls and a good part of the keep.

As far as religious architecture is concerned, the Pieve dei Santi Stefano e Degna and the marvellous Church of Santa Maria Maddalena are worth a visit. If you love art, don’t miss the Sala d’Arte San Giovanni, which houses works of great value.

An important hamlet in the municipality of Castiglione d’Orcia that I recommend you visit is Bagni San Filippo. This small village is a real jewel of the Val d’Orcia, thanks above all to its thermal complex. The thermal waters of this area have been known since ancient times for their beneficial properties and even today are a meeting point for travellers and citizens alike.

The town is small but very characteristic. Its landmark building is the famous Church of San Filippo, once located at the top of the village. However, the real centre of the town is the thermal spring. Being completely immersed in nature, it offers breathtaking scenery and is able to transport you to another, almost fairy-tale atmosphere. The calcium formation, called the “White Whale” because of its shape, is also worth seeing. In short, those who want to relax around Pienza can do so with these fantastic spas!


What to do near Pienza Tuscany?

Nature and sports enthusiasts can enjoy walking, cycling or horse-riding in the wonderful hills of the Val d’Orcia.

We conclude with the food and wine on offer, with traditional dishes such as Tuscan buccellato, wild boar stew and ricotta soup, paired with a local wine called “Ripagrande”.

If my article on Pienza and its surroundings has convinced you, don’t waste time and choose the most suitable experience for you with Italia Delight! You will also have the possibility to customise your trip with a Local Expert! What are you waiting for? 😉


About Author

Matteo Panella
Ciao, sono Matteo Panella! Sono un giovane ragazzo romano di 22 anni, appassionato allo sport e al mondo del cibo e della cucina, attualmente iscritto alla facoltà di Scienze e Culture Enogastronomiche dell’Università Roma Tre.


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