Tuscany is a beautiful, vast, rich and surprising region and no individual post, article or guide can do justice to its charming complexity. You could visit it a thousand times, picking a thousand different routes and never run out of fascinating new corners to explore and local delicacies to taste. We have already featured some of our favourite Tuscan destinations in a previous article and we will probably suggest plenty more in the future. Right now, however, we happen to be in love with one particular area of Tuscany, in which one of our latest team-building projects was set and we feel an overwhelming need to share our passion with you. Val d’Orcia is a beautiful valley, encompassing the province of Siena and part of the province of Grosseto, in the southern part of Tuscany. In Val d’Orcia you will be overwhelmed by the beauty of the scenery and enthralled by the charm of quaint little villages, retrace the steps of great artists of the past and contemporary award-winning directors, experience the intimate spirituality of ancient abbeys and feel the proud might of medieval castles, sample traditional recipes and sip exceptional wines. History, nature and culture create the luscious texture of this land. In this article, you will find our pick of the region’s sights.
1. San Quirico D’Orcia, a stroll through history
This is an ancient village, whose earliest settlement is believed to be Etrurian. San Quirico is not among the most popular tourist destinations not because it lacks in natural and architectural beauty, but simply because the competition is frankly insane. Despite its less than impressive size, this village has several notable features, including the medieval Vignoni Castle, a number of ancient churches and two magnificent renaissance gardens known respectively as Horti Leonini and The Rose Garden. Both are located along the town’s high street. The fraction of San Quirico known as Bagno Vignoni is famous for the large thermal bath around which the whole hamlet was built. What is effectively a broad pool occupies the place that one would normally associate with the town square.
2. Rocca D’Orcia, where time has stopped
Like San Quirico, this small town, also known ad Rocca a Tentennano, is of Etrurian origin. To be fair, there is little in the whole area that can be said not to be of Etrurian origin. Historically, this was a fortified settlement of strategic importance, because of its elevated position that made it easy to defend and allowed the occupants a clear view of the roads leading to and from the whole valley. As historical changes caused the fortress to become less strategically relevant and the nearby village of Castiglione to replace Rocca D’Orcia as the political and commercial epicentre of the area, the town was gradually abandoned and therefore left intact. This makes for a unique, timeless condition, whereby the original village buildings have been restored and no new ones have been built.
3. Montalcino: Rosso or Brunello?
This is where the celebrated wine by the same name is manufactured and it is therefore not surprising that wineries be such a common sight in the streets of Montalcino, even more so than in the rest of Tuscany. Among the many spots that host the typical eateries and bars in which you could sit and enjoy a glass excellent red wine, the fortress is probably the most popular and definitely the one with the grandest view. Looking down, you will be able to “drink in” the entire valley in all its glory. If you take a stroll down the main street and to the central Piazza del Popolo, you’ll notice the high tower of Palazzo dei Priori, a late-medieval building that nowadays houses the city council. When you pick your favourite winery and sit down to enjoy a local red, be sure to try both the specialities for which Montalcino is famous: Rosso and Brunello. The main difference between the two varieties is ageing. While a Brunello is required to age for a minimum of five years, two of which in oak casks, a simple Rosso only needs to age for one year, making for an altogether lighter – and often less pricy – choice. When in Montalcino, we recommend you visit the Abbey of St. Antimo, a perfectly preserved romanic church whose origins are the stuff of legends. It is unclear who built this place of worship, but it is said to date back to the age of Charles the Great.
4. Monticchiello: dream of Tuscany, wake up here
If you have an abstract idea of a quaint medieval town in Tuscany, it probably looks like Monticchiello. Imposing, fortified walls enclosing a maze of narrow alleys dotted with tiny workshops, a whole architectural system revolving around the town square, in which social occasions and cultural events usually take place. If you visit over the summer, for instance, you might happen upon a local theatre production, the popular “Teatro Povero”, which is entirely staged by local residents who are not professional actors. It is worth noting at this point that the population of Monticchiello rarely exceeds 200 people. The Church of Ss. Leonardo and Cristoforo is undoubtedly the town’s most notable landmark, dating back to the XII century and restored in the XVIII century and later again in 1933. The last restoration focused particularly on the original frescoes, only eight of which remain intact.
5. Pienza: the ideal renaissance city
This is the largest town in the valley and its centre has been a listed Unesco World Heritage Site since 1996. The current structure of Pienza is heavily influenced by the construction and restoration work ordered during the Renaissance by Pope Pius II, who aimed to turn it into the ideal of a perfect city. This involved urban planning that was astoundingly advanced for the XV century and resulted in the city having a larger concentration of landmarks than any other in the area. The Cathedral is a masterpiece of Renaissance architecture and contains several paintings from the renown Senese School. Other notable sights include the Palazzo Vescovile (the Bishop’s residence), the Palazzo Comunale (housing the city council) and Palazzo Piccolomini. Nowadays, Pienza is also well known for the local pecorino cheese, a delicacy that you will be able to sample at the local eateries or visiting one of the farms that produce it. It tastes delicious with red wine, but that goes without saying.