Exploring the rolling wheat or vineyard covered landscapes of southern Tuscany
When you picture Tuscany and you see rolling green hills with a lone cypress at the top or gentle yellow covered hills with rolls of haystacks spread across the fields, you are picturing the breathtaking landscapes of the Val d'Orcia valley in southern Tuscany. Medieval castles, hilltop towns, charming rural farmhouses, rows of vineyards or of cypress trees and golden wheat fields are just some of the elements that complement the fantastic landscapes of the Val d'Orcia!
The Val d'Orcia is a valley crossed by the Orcia river, from which the valley derives its name. This wonderful region in southern Tuscany stretches across the province of Siena to its north and reaches Grosseto to the west. The area is now protected as a natural and cultural park, and it has been recognized as a World Heritage Site by UNESCO since 2004. Beautiful nature is the actual absolute protagonist in Valdorcia, with many different colors according to each season.
The impressive views of Val d'Orcia, which inspired so many Renaissance painters, is dotted with many little villages, castles, abbeys and hamlets, each telling a fascinating ancient history. Time here can still pass slowly and you can enjoy every second of it. This region is also very rich in high quality local products such as the red wines of Bruncello di Montalcino and the Vino Nobile di Montepulciano, as well as the Rosso d'Orcia, "pecorino" cheese from Pienza (a Tuscan cheese made from sheep's milk that grow and feed in the surrounding hills), genuine olive oil, saffron, mushrooms, chestnuts, truffles, game and many other specialties.
If you only have a day to explore the Val d'Orcia, here is how we recommend you organize your day. Depending on where you start, you can follow the itinerary in the order presented or in reverse order. I will assume you start in Siena, therefore making your way down the ancient Via Cassia is the best way to start. I'm also assuming you're traveling by car, although the area can also be visited by joining a guided tour (such as this one). Also, I've suggested "side detours": if you have more time on your hands to explore the area, these are additional stops in the area we'd recommend you visit but adding stops will surely not make it easy to see everything in just one day.
Buonconvento & the Crete Senesi
Heading down the Via Cassia (SR 2) you will actually be following the ancient Via Francigena road down to Rome, and first passing through the Crete Senesi area. This area is characterized by clay hills that formal a surreal landscape, often described as "lunar" in some ways. It is a spectacular landscape and since you're in the area, why not take the panoramic route, right? You will start seeing the green hills from Monteroni d'Arbia down and will find several points where you can stop and take photos.
Your first stop is Buonconvento, a small medieval walled town considered among one of the most beautiful villages in Italy. It was a stop for travelers along the ancient Via Francigena but was also an important center for trade in the area. Time seems to have stopped inside the walls with its historical, red brick buildings standing tall. We recommend just a quick stop here to walk around before continuing on.
⇒ Side Detour: Abbazia di Monte Oliveto Maggiore
⇒ See also: An itinerary to explore the Crete Senesi
After Buonconvento, you enter into the Val d'Orcia area: there are few other places that are able to impress the traveler so deeply. It is almost a surreal and suspended land, which is home to the most precious and appreciated Italian wines: the Brunello di Montalcino, the Nobile di Montepulciano, the Rosso Orcia, and other superb and fine wines with the protective DOCG denomination. Our second stop is Montalcino, the city of Brunello.
You'll arrive into town right by the old fortress, or Rocca, from the 14th century. Stop and visit inside to climb the ramparts and enjoy the incredible view of the surroundings. Then head down into the center of town to admire the slender clock tower - try to not be distracted by all the wine shops and offerings of wine tastings ;-).
⇒ Side Detour: Abbey of Sant'Antimo
A must-see is the beautiful and suggestive Romanesque Abbey of Sant' Antimo, one of the best examples of medieval monastic architecture; here you can really breath a mystic and medieval atmosphere and listen to beautiful Gregorian chants during mass. When kissed by the sun, the magnificent travertine stone facade of the abbey shines with golden reflections.
⇒ Love wine tasting? Try our wine route around Montalcino to taste the Brunello di Montalcino
San Quirico d'Orcia
Next stop is San Quirico, but be prepared to stop shortly before you arrive in town: a perfect photo opportunity of the classic Val d'Orcia landscape presents itself along the Via Cassia road. You're likely to see the most-photographed copse of cypress trees in all of Tuscany right along the road as well as many other cars stopped off the road - make sure to stop yourself!
Then park around the walls of the medieval town of San Quirico, another town along the Via Francigena which spelled its good fortune through the ages. Here, take a walk inside and admire the beautiful Collegiata of the Saints Quirico and Giulitta, the Horti Leonini gardens and just walking along the main street in times past with its ancient center. Either San Quirico or Pienza make great stops for lunch, since there are several restaurants offering local specialties.
As you head toward Pienza, again you'll find another photo-opportunity: the Cappella Vitaleta is the small tiny chapel you likely have seen in many photos of Tuscany.
⇒ Side Detour: Bagno Vignoni
You can relax in one of the many thermal baths of the region, the closest one being Bagno Vignoni. The heart of Bagni Vignoni is quite magical: you'll find an absolutely unique tiny hamlet with a series of ancient buildings all surrounding the central Renaissance-era swimming thermal water pool with its beautiful arcades. While the pool is no longer open to the public, Bagni Vignoni and its spas are perfect for a relaxing holiday, far from the crowds. If the weather is right, you could sit and stick your feet in the warm water springs as it makes it way behind the main piazza and down the hill.
The small hilltop village of Pienza is a real jewel known as the "Ideal City": a unique Renaissance monument designed by the great humanist Pope Pius II, with its narrow winding streets and the beautiful Palazzo Piccolomini which belonged to the pope's family. The palazzo itself merits a visit, as well as the cathedral and town hall that surround the main square, all built to represent how man could build the ideal city around himself. One of the main attractions of this small town is the pecorino cheese, so make sure to stop by the shops and do some taste testing ;-) Make sure to also walk around the walls behind the cathedral to enjoy amazing views of the Val d'Orcia as far away as Monte Amiata.
⇒ Side Detour: Montichiello
A small medieval walled village to the south of Pienza that will give you additional great views of the area and of cypress lined roads.
While Montepulciano is no longer in the Val d'Orcia valley, it is so close by that a visit cannot be avoided! A visit through the town is a must - making your way uphill through its walls and along its streets as they make their way up to Piazza Grande. Here, the Palazzo Comunale is the largest building to draw your eye (and which you can climb to see the views of the surrounding hills) but the Duomo and surrounding palaces also merit your attention. If you still have the time and energy, head down to San Biagio below the town: standing in perfect isolation in the middle of the countryside, this mighty pilgrimage church in travertine stone offers several of the best examples of Renaissance architecture.
⇒ Love wine tasting? Montepulciano is also famous for its Vino Nobile di Montepulciano as well as Rosso di Montepulciano, so you can either visit the wine shops in town or head out to follow a wine tasting itinerary around Montepulciano.
Don't have a CAR but still want to visit Val d'Orcia?
Another Val d'Orcia itinerary through wine tasting
Another way to organize your travel through the Val d'Orcia is through wine tasting: follow our Val d'Orcia wine road itinerary.