A weekend in Val D'Orcia, Tuscany

Apr 26, 20236 min read

Val D'Orcia is a region in Tuscany that is home to the Brunello wine region, Medieval towns, and some of the most picturesque driving routes in Tuscany. It is located in the south of the Siena province and stretches across five districts and countless small villages.

The idyllic cypress tree-lined winding roads and my love of Brunello wine drew me to this region and it did not disappoint. There are many towns and vineyards to visit in the area and I recommend booking if you would like to take a tour or eat in any of the popular destinations as they get booked up during the busy months. As Val D'Orcia is known for its beautiful roads I recommend hiring a car for the weekend to get the best out of your trip.

I spent a long weekend exploring Val D'Orcia by car and visited the towns of Montalcino, San Quirico d'Orcia, Pienza, and Montepulciano. However, there are also many other towns to visit including Bagno Vignoni and Bagno San Filippo. I've put together a weekend itinerary full of recommendations for your next weekend getaway!

Weekend itinerary
Where I stayed
Where I ate
Favourite wines I tasted

A weekend itinerary for Val D'Orcia

Day 1 - Exploring the towns of San Quirico D'Orcia, Pienza, and Montalcino!

San Quirico D'Orcia

I started my journey by driving to the small hilltop town of San Quirico D'Orcia.

Although the town is small it is steeped in history as it was an important stop along the pilgrimage route, the Via Francigena, that connected northern Europe to Rome in medieval times. Walking around you can see the town's old fortified walls, charming narrow streets, and the main square which is a lovely spot for a coffee to admire the Church of San Francesco. The Horti Leonini gardens are also worth visiting, just off the main square, a beautiful classic Italian garden that offers views over the Tuscan hills.

San Quirico panoramic views

San Quirico town and Horti Leonini Gardens

SP146 Road to Pienza

After a walk around the gardens and a quick coffee, I left San Quirico D'Orcia to drive along the SP146 to Pienza.

The road that links these two towns is one of the most picturesque and most photographed roads in Val D'Orcia. Lined with cypress trees and unparalleled views of the valley on either side of the road it is a beautiful 15-minute drive. The panoramic road offers breathtaking views of the surrounding countryside and passes many picturesque spots including the Cappella della Madonna di Vitaleta, a tiny secluded chapel surrounded by cypress trees, and the Gladiator Shooting Spot. There are many places to stop for photos along the road, but you may have to fight an influencer for the best spot at busy times!

Views from the SP146

Pienza

The panoramic SP146 road brings you to the small town of Pienza.

As you walk through the streets of Pienza you notice the beautiful Renaissance architecture straight away and understand why it has been declared a UNESCO World Heritage site. In the town, you will find many restaurants and shops where you can taste Pecorino di Pienza, the town's very own pecorino cheese! As pecorino is one of my favourite cheeses I had to stop in this beautiful town for lunch and to taste the famous cheese myself.

I ate lunch on the beautiful terrace of Terazza Della Val D'Orcia which has stunning views over the rolling Tuscan hills and great food to match. Pienza is the perfect spot for lunch as after eating too much cheese you can walk it off around the small streets and browse the local shops.

Views from Terazza Della Val D'Orcia in Pienza

Castello Banfi Wine Tour

After a lovely lunch, I drove back towards my hotel in Montalcino along La Maremmana Strada to Castello Banfi for a wine tour before dinner!

There are many places to choose from when selecting where to do a wine tasting in Val D'Orcia. Castello Banfi was a great option due to its beautiful surroundings and well-known Brunello wines. The tour took us to the location where they pick the grapes and produce the wine, then to the room where they age the wine in barrels, and then finally to the cellar where we tasted a variety of different wines paired with cheese and dried prunes. The castle itself is breathtaking and the views surrounding definitely worth a picture!

View from Castello Banfi

Castello Banfi Wine Tour

Dinner in Montalcino the city of Brunello Wine

A trip to Val D'Orcia would not be complete without a visit to Montalcino where the famous Brunello di Montalcino red wine is produced!

Montalcino is a beautiful hilltop village made famous for it's Brunello red wine and breathtaking views. When you reach the top of the stairs from the car park to the town centre a view over the Tuscan valleys, vineyards, and cypress trees awaits you. The village is surrounded by fortified walls and is relatively small to walk around. However, it is definitely worth visiting as it is a great place to try the local red wines and purchase wine from the local wine shops.

There are many amazing places to eat in the town of Montalcino, but I opted to eat in a restaurant just a few minutes drive outside of the village called Baccon Di Vino. When you first enter the restaurant the floor-to-ceiling windows looking out onto the stunning views of the countryside instantly take your breath away. When I visited in August the sun was setting as soon as we sat down around eight pm which turned the rolling hills into a beautiful pink hue. Not only was the view incredible, but so was the food and wine! The food had a wonderful fine dining feel to it while still remaining classically Italian. Paired with a Bible of Brunello red wines to choose from Baccon Di Vino quickly became my favourite restaurant in Tuscany.

Town of Montalcino

Sunset views from Baccon Di Vino

Day 2 - A beautiful lunch spot and a quick stop in Montepulciano

Lunch at Il Passaggio Capanna Suites

After spending a relaxing morning in the Agrotourism Hotel I drove to the restaurant Il Passaggio Capanna Suites.

I wanted to lunch in Il Passaggio before leaving Montalcino as Capanna is known for producing a wide variety of wines characteristic of the Montalcino region to a high standard. The delicious wine and food were made even more spectacular as I sat on the terrace overlooking the sunny village of Montalcino and the surrounding vineyards. The restaurant is worth a visit for anyone going and you can even stay there too!

Il Passagio Capanna Suites

A quick trip to Montepulciano

As Montepulciano is only a 40-minute drive from Montalcino I had to take a look around one last Medieval town before leaving the region.

When visiting you have to park in the lower part of the town and enter by Porta al Prato. After a short uphill walk, you reach Piazza Grande which sits at the heart of the town. Walking around you will see many Renaissance palaces, artist workshops, and panoramic viewpoints to look over the Val D'Orcia region. Piazza Grande is the perfect place to sit with a glass of the famous Vino Nobile di Montepulciano and watch people pass by.

This hilltop town was the perfect ending to a stunning weekend exploring Val D'Orcia!

Renaissance architecture of Montepulciano

Where I stayed when visiting Val D'Orcia

When exploring the region I chose to stay close to Montalcino in a lovely agrotourism hotel called Podere Brizio. The majority of places to stay in the region are working vineyards, called Agrotourism, which are full of character and amazing Brunello wine! I stumbled open this agrotourism stay by chance and it made my trip. The rooms are spacious and full of character with stunning views across the rolling hills of Val D'Orcia. The first night we stayed at Podere Brizio we checked in and went straight out to dinner in Montalcino. At dinner, we were presented with an extensive Bible of Brunello wines so we asked the restaurant owner's advice to decipher which of the many wines to choose from. Much to our surprise, he said his favourite wine was Podere Brizio's Brunello di Montalcino! After that, we were sold and Podere Brizio became a highlight of the trip.

I chose to stay near Montalcino due to its central location in visiting other towns in the region and its choice of Agrotourism. However, there are many other great places to stay depending on your needs. Many towns have hotels in the centre and there are also many options for Agrotourism in the surrounding vineyards. Options of other towns to stay in are San Quirico D'Orcia and Pienza.