Start again with us Discovering Val D’Orcia

Start again with us Discovering Val D’Orcia

When we say the word Tuscany what comes to your mind? Imagine yourself or your customers comfortably seated in a minivan heading to one of the best wineries in the middle of the Tuscan hills. Nature, Relax and Happiness, are the keywords of a holiday in Val D’Orcia the land of the Brunello wine.

We thought we would give you some useful information to help you find out the enchanting valley. We’ll start with Montepulciano and continue to Montalcino, passing through Pienza and San Quirico d’Orcia. A panoramic journey through history, art, good food and excellent wines, just waiting to be experienced.


Montepulciano is a small medieval town a few kilometres from Siena that offers a magnificent view of all the surrounding hills. Its Renaissance palaces, ancient churches and splendid squares are famous. It is by walking through its streets that you can discover the city and its hidden treasures. Most of the shops and restaurants can be found on the main street, which stretches from Porta Al Prato to Piazza Grande for 1.5 kilometres, the highest point of the city dominated by the Palazzo Comunale, the town hall designed by Michelozzo and reminiscent of the Palazzo della Signoria (Palazzo Vecchio) in Florence. (It was Cosimo I de Medici who commissioned the construction of the Palazzo Comunale in Montepulciano, designed in a very similar way to the Palazzo Vecchio in Florence, to indicate its dependence on the Florentine city) Also noteworthy are Palazzo Contucci and Palazzo Tarugi, former homes of the area’s nobility, and the Museum of Torture, where you can see a private collection of instruments used to inflict pain dating back to medieval and Renaissance times.

Strolling through the alleys of the centre you will find many historic cellars offering tastings of Nobile, the famous DOCG wine produced only in Montepulciano, accompanied by typical products of the highest quality. We can help you personalize your day including one wine tasting in one of the most famous cellars in the area.


A UNESCO World Heritage Site, Pienza is considered the ‘touchstone of Renaissance town planning’ for its history, art and culture. The trapezoidal Piazza Pio II is bordered by four buildings. The main residence, Palazzo Piccolomini, is on the west side with its hanging garden, which you can admire in the courtyard of the palace, the first hanging garden of the Renaissance. The Duomo dominates the centre of the square, whose architecture is a perfect blend of Gothic and Renaissance styles, and inside you can see works of art by some of the greatest artists of the Sienese school. The Bishop’s Palace is on the third side of the square and opposite the church is the town hall or Palazzo Comunale.

As in Montepulciano, here too you will find characteristic restaurants where you can taste the flavours of Valdorcian and Tuscan tradition, first and foremost the Pecorino di Pienza DOP, which you will find in many delicious and original variations that bring out its best qualities. Along the road to San Quirico d’Orcia, you must stop to admire the Cappella della Madonna di Vitaleta, a small church protected by cypress trees in the middle of the Vitaleta hills. A UNESCO World Heritage Site, this little chapel is also linked to a legend. It seems, in fact, to have been built on the exact spot where Mary appeared to a shepherdess to tell her to go to a workshop in Florence where she would find the statue to be placed in the church of Vitaleta.

San Quirico D’Orcia

San Quirico d’Orcia is also a small village surrounded by medieval walls, although its history is lost in the centuries up to the Etruscans. Its walls date back to the 15th century and still retain a dozen towers in good condition, incorporated into more recent buildings. About the original historic gates, however, only the Porta dei Cappuccini can be admired, with its unusual polygonal structure. San Quirico is fascinating and there are many things to see and do. Here are some things not to be missed.

In the centre of town you will find the Romanesque Collegiate Church and next to the Porta Nuova you can admire the Horti Leonini. This is an example of the asymmetrical Italian garden. The area covered by the Horti is 13,824 square metres and is spread over two levels.A statue of Cosimo III de’ Medici built-in 1688 has been placed in the centre of the garden. There is also a rose garden, which occupies a small space in front of the parish church of Santa Maria, located near the edge of the Horti Leonini. 

The cypresses of San Quirico d’Orcia are the most photographed trees in the world! Cypresses are a symbol of Tuscany and, in particular, a characteristic of the Val d’Orcia. They are two distinct groups of trees, situated on isolated hillsides overlooking the southern part of the Via Cassia.  If you want to take a look at this iconic landscape open these google maps links below:

1 Cypresses San quirico 

2 Cypresses San quirico


Montalcino is a jewel of history and art, hidden deep in the hills of the Val D’Orcia. This medieval town will welcome you through its straight and steep streets with breathtaking views. Montalcino is also known as the town that produces Brunello di Montalcino, one of the world’s most famous wines made from the Sangiovese grape. After you reach the highest point of the town, you will be treated to an incomparable view of the Sienese hills dotted here and there with olive trees, oaks, cypresses and small country lanes.

Enjoy the view and don’t miss the Rocca, a 14th-century fortress that dominates the historic centre: from there you can admire Monte Amiata and the Crete Senesi, as well as the entire Val d’Orcia and the Maremma hills.



Once in the area, it is absolutely worth visiting the beautiful Abbey of Sant’Antimo, a former Benedictine monastery located in Castelnuovo dell’Abate, in the municipality of Montalcino. A monumental 13th-century structure and one of the best examples of French Romanesque in Italy. The area around Montalcino with its vineyards, olive groves and dense forests is not only part of the world’s imagination but has also contributed to the recognition of the town itself and the entire Val d’Orcia as a World Heritage Site.

San Giovanni d’Asso, which stands on high ground, also belongs to the territory of Montalcino. Its castle is certainly its distinguishing feature, with its red brick providing a surprising welcome. This small town represents an area of great gastronomic quality with its Truffle Museum, the first in Italy dedicated to the precious and fragrant tuber. A visit to this museum is a mouth-watering journey through the five senses, with a banquet of exhilarating smells that help you really get to know this wonderful food and get in tune with the whole territory.

These are just some of the curiosities and information about one of the most famous and charming areas of Tuscany in the world, which is also a stage of the Giro d’Italia last 19 May.

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