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A Drive Through the Val D’Orcia: Experiencing La Dolce Vita in Tuscany!

A drive through the Val d’Orcia should be high on your list of things to do when visiting Tuscany.

Designated a UNESCO World Heritage Site, the Val d’Orcia is ridiculously scenic. And a drive through the region is the perfect way to experience la dolce vita in Tuscany! Read on to discover the ultimate one-day itinerary for a drive through the Val d’ Orcia.

Landscape in the Val d'Orcia Tuscany Italy

The Val d’ Orcia loosely refers to the part of Tuscany south of Siena, all the way to Monte Amiata. Driving through the Val d’Orcia, you’ll see those trademark Tuscan rolling hills and marching rows of cypresses. The scenery is the main attraction here, but the region is also known for its delicious food and wine.


You could easily spend many days enjoying the beauty and serenity of the region. But you can certainly see most of the highlights of the Val d’Orcia in one day. It’s an easy self-drive route. But if you want to focus on the views around you (and the wine!), then opt for a guided tour. Or hire a car and driver, to follow the itinerary you map out.

San Quirico d' Orcia Tuscany Italy

For this Val d’Orcia itinerary, you’ll start and end the drive in Siena. Start early in the morning, because the landscape looks its prettiest in the mellow light of early morning and late afternoon.

Siena to Asciano and the Crete Senesi

Driving Distance: 31.3km Driving Time: About 40 minutes

From Siena, take SS73 to SP438 and drive to Asciano, a little hill town steeped in history. This part of Tuscany, south-east of Siena, is called Le Crete, or the Crete Senesi, after the famous gray clays of the region. The clays are sediment from the ancient Pliocene Sea, which covered the area millions of years ago.

The landscape is stunning, so you’ll want to stop often to take photos. You’ll see gently rolling hills dotted with small patches of woodland. Single farmhouses are surrounded by rows of cypresses snaking across the landscape.

Val d'Orcia Tuscany Italy

When we visited in the fall, after the harvest, much of the land was completely bare, and it was easy to understand why this landscape is described as lunar. At other times of the year, you may see it covered in green or gold, because wheat is cultivated here.

Shortly after you enter the Crete Senesi, pull over when you crest a hill for fabulous views of the surrounding countryside. On a clear day you will get a great view of the city of Siena. Then continue on to the little town of Asciano. Make a quick stop to view the Basilica di Sant’Agata. Then pop into Bar Herve di Manieri for coffee and a sweet treat before getting back onto the road.

Asciano to the Abbey of Monte Oliveto Maggiore

Driving Distance: 9.8km Driving Time: About 15 minutes

From Asciano, take SP451 to the Abbazia di Monte Oliveto Maggiore, a magnificent Benedictine monastery. The abbey is set in the midst of woods in the Crete Senesi region. It is a must-stop on your drive through the Val d’Orcia.

Abbazia di Monte Oliveto Maggiore Tuscany Italy

Although the Abbey was founded in the early part of the 14th century, construction continued through the following centuries. Admire the exterior, made of mellow red brick, before stepping inside.

Abbazia di Monte Oliveto Maggiore Tuscany Italy

In the Cloister Grande, view the 35 beautiful large frescoes celebrating the life of St. Benedict. The colors are vivid and the detail breathtaking. Some of the frescoes were done by Luca Signorelli, a Renaissance painter renowned for his work in the Duomo di Orvieto. The frescoes were completed by Antonio Bazzi, also called La Sodoma.

Frescoes in the Abbazia di Monte Oliveto Maggiore Tuscany Italy
Beautiful detail in a fresco at the Abbazia di Monte Oliveto Maggiore

Frescoes in the Abbazia di Monte Oliveto Maggiore Tuscany Italy

If you visit at the right time of day, you can listen to Gregorian chants by the monks in the abbey. Stop by the souvenir shop, where you’ll find herbal elixirs made by the monks of the Abbey! The abbey also produces wine and olive oil. Visit the tasting room to sample the wine. You can also visit the wine cellar underneath the cloister, with its big barrels of wine.

Wine cellar Abbazia di Monte Oliveto Maggiore Tuscany Italy

Entrance to the Abbey is free, but there’s a fee for parking.

Abbey of Monte Oliveto Maggiore to Buonconvento

Driving Distance: 9.2km Driving Time: About 15 minutes

From the Abbey of Monte Oliveto Maggiore, continue on SP451 to Buonconento, another of Tuscany’s pretty little towns. Surrounded by medieval walls, the town has served as a stop for travelers for centuries.

Similar to Siena, the little town is divided into districts, each with its own flag. Take a walk through the main street. Admire the old buildings and take in the charming medieval atmosphere.

Buonconvento to Montalcino

Driving Distance: 13.6km Driving Time: About 15 minutes

From Buonconvento, take SR2 to SP14 to the hill town of Montalcino. Montalcino is one of three major hill towns on your one-day Val d’Orcia itinerary. It is located on a hill, with commanding views of the surrounding countryside.

Montalcino in Tuscany, Italy

Walk around the pentagon-shaped fortress. It is reported to have held its own against the armies of Siena and Florence, when they attacked the little town.

Fortress Montalcino Tuscany Italy

Today the town is famous for its Brunello di Montalcino wine, made from Sangiovese grapes grown in area vineyards. Wander around the town, stopping to admire the warm colors of the buildings on both sides of narrow streets. Take in the views of the surrounding valleys, covered with vineyards and olive groves.

Montalcino Tuscany Italy
Warm colors in a street in Montalcino

Montalcino Tuscany Italy

Take a break for lunch. Try Alle Logge di Piazza, a trattoria located in the Piazza del Popolo in town. Sample a dish featuring the local pici pasta.

Montalcino to the Sant’Antimo Abbey

Driving Distance: 9.8km Driving Time: About 12 minutes

From Montalcino, drive south on SP55 to the Abbazia di Sant’Antimo, a wonderful example of Romanesque architecture. Founded in the 9th century, the Abbey of Sant’Antimo grew to be a rich and most powerful institution before eventually falling into decline.

Abbazia di Sant'Antimo Tuscany Italy

The abbey is set in the midst of olive groves and vineyards. It’s a location difficult to beat for beauty and serenity. The building is gorgeous, and it is difficult to believe that it had decayed to the point of being used as a stable before the Italian government restored it in the late 1800s.

Here too you can listen to Gregorian chanting by the monks of the abbey. The grounds are lovely. A large lone cypress stands by the building and there is a pomegranate tree in the back. Wander the grounds and the beautiful garden before stepping into the light-filled, airy interior.

Abbazia di Sant'Antimo Tuscany Italy

The interior is beautiful in its simplicity. Watching the play of light on the rustic wood, columns, and walls in the silence of this abbey was one of the highlights of the day for me.

Abbazia di Sant'Antimo Tuscany Italy
Beautiful interior of the Sant’Antimo Abbey

Abbazia di Sant'Antimo Tuscany Italy

For a special experience, invest in the “Path of Light” tour with video guide. As part of this tour, you will see the pharmacy in the monastery and the herb garden, where the plants that go into the monastic elixirs are grown. Definitely stop by the Farmacia Monastica store to browse the inviting products available for purchase. You can buy local honey, preserves, teas, and beauty products made from herbs and plant essences.

Sant’Antimo Abbey to San Quirico d’Orcia

Driving Distance: 14.2km Driving Time: Around 15 minutes

From the Abbazia di Sant’Antimo, take SP14 to SR2 to the small medieval town of San Quircio d’ Orcia. Perched on a hilltop, San Quirico d’Orcia is charming. Walk around the town and step inside the little Church of San Francesco. This church is now home to Andrea della Robbia’s statue of the Madonna that previously used to reside at the famous Vitaleta Chapel just outside the town. Explore the Horti Leonini geometrical gardens. From the city walls, you get magnificent views of the Val d’Orcia.

San Quirico d’Orcia is beautiful in its own right, but it’s also famous for being close to two of the most photographed spots in Tuscany.


The Cypresses of San Quirico d’Orcia are probably some of the most photographed trees in the world. They are located on a hillside and accessible from the road going from Montalcino to San Quirco d’Orcia, just near the long bridge. We got out of the car and walked over the field to get close to the copse of trees.

The Cypresses of San Quirico d'Orcia, Tuscany. Italy

The second icon is the tiny Capella della Madonna di Vitaleta, a UNESCO World Heritage Site. This beautiful little chapel set in the midst of the Tuscan countryside is one of the most photographed sites in Tuscany. We only saw it from a distance, from the main road leading from San Quirico d’Orcia to Pienza.

The Vitaleta Chapel in the Val d'Orcia Tuscany Italy

San Quirco d’Orcia to Pienza

Driving Distance: 9.8km Driving Time: About 15  minutes

From San Quirco d’Orcia, take SP146 to Pienza. This is one of the most beautiful roads in the region with picture postcard Tuscany views on all sides. Undulating hills, rows of stately cypress trees, the occasional farmhouse, and fields as far as the eye can see!

Pienza was declared a UNESCO World Heritage Site in 1996. Prior to our visit to Italy, when I was researching our trip, I had read a lot about the beauty of Pienza. My expectations heading into Pienza were therefore sky-high, and the first view of the pretty hill town did not disappoint.

Pienza was originally called Corsignano. It is the creation of Piccolomini, who became Pope Pius II. He wanted the town of his birth to become the “ideal” Renaissance town, and invested the money to transform it. Worth seeing are the Duomo di Pienza, the Piccolomini Palace, and the main square, the Piazza Pio II.

Pienza Tuscany Italy

In Pienza, we enjoyed our obligatory daily gelato break at Fredo, a charming little gelateria offering gelato artigianale.

Pienza Tuscany Italy


Pienza is famous for its pecorino cheese, which can taste from mild to assertive depending on how aged it is. The little shops sell pecorino, olive oil, local wines and pici, the local pasta. Wander the streets, pausing to take in views of the surrounding countryside, and browse the little shops.

Pienza Tuscany Italy

Pienza to Montepulciano

Driving Distance: 14.3km Driving Time: About 20 minutes

From Pienza, take SP146 to Montepulciano, the final stop on your one day Val d’ Orcia itinerary. Strictly speaking, Montepulciano is located in the Val di Chiana. But Montepulciano is too stunning to not include in your itinerary for a drive through the region!

Montepulciano Tuscany Italy

With its narrow uphill streets and beautiful palaces, Montepulciano is one of the loveliest hill towns in Tuscany. From the Porta al Prato, make your way on Via Roma to the piazza where you can see the Colonna del Morzocco, the Column of the Florentine Lion.

Colonna del Marzocco Montepulciano Tuscany Italy

The Corso, the main street, winds uphill all the way from the town gate to the main square at the top of the hill. Browse the little shops along the streets of Montepulciano, with their wares of local wines, pastas and cheeses. We picked up some of the rich local olive oil we had tasted at lunch, to take back home. Taste some Tuscan wine: Montepulciano is famous for its red wine, the Nobile di Montepulciano.

Montepulciano Tuscany Italy

If you have the time, walk to the lovely Church of the Madonna di San Biagio, located below the city walls on a hillside. The church is known for its acoustics. Stand on the marked oval and clap or sing to experience the magic.

Basilica of San Biagio in Montepulciano in Tuscany Italy

Montepulciano to Siena

Driving Distance: 60.8km Driving Time: About 55 minutes

From Montepulciano, take SS73 (or SP438 through the Crete Senesi) back to Siena. If you’re like me, you’ll want to stop for some final few photos of the beautiful countryside in the last light of the evening.

So there you have it: my one-day itinerary for a fabulous scenic drive through the Val d’Orcia. It is one of the best day trips from Florence you can do! If this drive ignites a desire to explore more villages and towns in Tuscany, check out this list!

If you have done this drive, I’d love to know if you have additional suggestions to make this itinerary even more amazing. And if you haven’t done the drive yet, make sure you add it to your list for your next visit to Tuscany!

If you are visiting Rome and your time in Italy is limited, you can still get a taste of la dolce vita in the Val d’Orcia with a guided small-group tour! The Tuscan Hilltowns, Fortresses & Vineyards day trip from Rome by Take Walks is highly rated, and includes a visit to Pienza, the Montalcino fortress, a local farm, and a vineyard for wine tasting. We did two tours by Walks of Italy on our first visit to Italy and loved both!

From Siena, you can do this highly rated small group tour that will take you to Pienza and Montepulciano, and from Florence, you can check out this highly rated food tour of Pienza, Montepulciano, and Montalcino!

Looking for other scenic drives in Italy? Check out my post on driving Italy’s spectacular Amalfi Coast. For other great things to do in Tuscany, read my suggestions for how to spend one perfect day in Siena, or the top ten things to do in Florence on your first visit.

How to Spend Two Perfect Days in Venice
Cinque Terre: Two Days in the Cinque Terre — What to See, Do and Eat!
Capri: One Day in Capri — What to See and Do
Rome: 25 Best Things to Do on Your First Visit to Rome
Orvieto: One Day in the Charming Umbrian Hilltown of Orvieto
Lerici and Portovenere: Two Charming Ligurian Coastal Towns You Must Visit

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Discover the perfect one day itinerary for the scenic drive through the Val d'Orcia in Tuscany, Italy!


Dhara's travel interests are eclectic, spanning everything from natural wonders to history, culture, art and architecture. She has visited 22 countries, many more than once, plus almost all 50 states of the USA, and has amassed a hoard of cherished travel moments.

8 thoughts on “A Drive Through the Val D’Orcia: Experiencing La Dolce Vita in Tuscany!”

  1. Thank you Dhara for a wonderful post. I am green with envy after reading all the information, and looking at your delightful photos, of your beautiful Tuscan day trip. I most definitely want to return to Italy. I am very interested in your comment about hiring a driver for the day. I would appreciate any details about how you find a driver for the day, cost, language difficulties etc etc. Perhaps you could add these details to the blog, as I’m sure I wouldn’t be the only one interested.

    • Thanks so much Estelle. It is a wonderful area for a drive. I just asked the hotel where we were staying and they arranged the car and driver for us. Our hotel in Sorrento arranged for a car for us for our Amalfi Coast drive as well, so that would be my suggestion!

  2. Thoroughly enjoyed this post especially as we still have much of Italy to discover. Particularly love the photos of the interior architecture of Abazzia. Totally incredible. The landscapes of course are pretty spectacular too. Really enjoyed this day in the Italian countryside with you.


    • Thank you so much. You cannot visit Tuscany without leaving a little piece of your heart behind…and the Val d’ Orcia is particularly scenic, with its abbeys and little hill towns. I do hope you have the opportunity to visit!

  3. Hello Dhara,
    Thank you for your suggestions! Did you have trouble finding parking in any of the stops along this itinerary? I’ve heard parking inside the wall of a villiage can be tricky and tickets are easy to get!

    • Hi Bethany, there are parking lots just outside the town walls at all the towns. You can Google the specific towns you want, to find them. You do not want to drive into the ZTL zones, but driving up to the public parking lots posed no problems for us.

  4. Such a great post! Did you just do a drive through or did you stop to walk around? If so, where did you park your car and how long did it take for the whole thing if you walked around?

    • Hi Emily, we walked around for about an hour or so in each of Montalcino, Montepulciano, and Pienza, had lunch, visited the two abbeys at leisure, made several photo stops, and did a few other quick-ish walks, and it took us about 9-10 hours, from Siena. You can park in designated parking lots outside each town, and then walk in. The parking lots should be obvious because the towns are small, but you can also consult your GPS when you are close or google them ahead of time and print out directions.


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