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

Like this article? Share it with your friends!

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
Val d’Orcia landscape PC: Shutterstock | Riska Parakeet

Some links on this page may be affiliate links. If you click an affiliate link and make a purchase, we may receive a small commission, at no extra cost to you. For more details, refer to our disclosure.

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 in the Val d’ Orcia, 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 for a private tour, and see if they will follow the itinerary you map out.

The Vitaleta Chapel in the Val d'Orcia, Tuscany, Italy
The famous Vitaleta Chapel

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.

Prefer to leave the driving and logistics to someone else? Check out these guided tours of the Val d’Orcia:

From Rome: This popular day trip from Rome includes visits to Montalcino, Montepulciano, and Pienza, with wine tastings and lunch at a Tuscan farm.

Book a full-day tour of the Val d’Orcia from Rome now!

From Florence: This wine and cheese guided tour from Florence makes stops at Pienza, Montalcino, and Montepulciano, and includes wine tastings at two area wineries.

Book a full-day tour of the Val d’Orcia from Florence now!

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
The rolling hills of the Val d’Orcia after the harvest

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
The Abbazia di Monte Oliveto Maggiore

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
A beautiful entrance at the abbey

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 cathedral in 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
A fresco at the abbey

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
The wine cellar at the abbey

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

Visiting Florence and prefer to join a guided tour? Consider this highly-rated full-day tour that includes Montalcino, Pienza, and Montepulciano, as well as wine and cheese tasting!
Book this tour of the Val d’Orcia now!

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.

Street in Buonconvento, Italy
Street in Buonconvento

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
The fortress in Montalcino

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
Walking through Montalcino

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 Sant Antimo Abbey

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
A pomegranate tree at the abbey

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
The interior of the abbey

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.

San Quirico d'Orcia, Tuscany, Italy
San Quirico d’Orcia

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 Cypresses of San Quirico d’ Orcia

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
The Vitaleta Chapel

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.

The Duomo in Pienza, Italy
The Duomo di Pienza

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

Pienza Tuscany Italy
Gelateria in Pienza


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
A small shop in Pienza

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 Column of the Florentine Lion

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
Walking the Corso in Montepulciano

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
The San Biagio Church is so picturesque!

And if you enjoy gardens and visit during months with long daylight hours, you may even be able to squeeze in a visit to the beautiful gardens at La Foce, about a 15-minute drive from Montepulciano.

While the gardens are gorgeous any time of the year, visit when the wisteria is in bloom for a truly sensational experience!

Note that the gardens can only be viewed on guided tours, which are offered on Wednesdays, Thursdays, and Sundays at the time of writing. If you wish to visit, check the La Foce website for current tour information.

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 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!

And if this drive ignites a desire to explore more villages and towns in Tuscany, check out this list!

A field in Tuscany
Landscape in the Val d’ Orcia

Guided Tours from Rome to the Val d’ Orcia

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!

Alternatively, consider this less expensive but super popular and well-reviewed tour that shows you the best of the Val d’ Orcia in one day. Visit Montalcino, Pienza, and Montepulciano, sample local wines, and enjoy lunch at a Tuscan farm.

Book this full-day tour to the Val d’Orcia from Rome now!

With a car or a guided tour, the beautiful Val d’Orcia makes for one of the most scenic day trips from Rome you can do.

Cypresses of San Quirica d'Orcia in Tuscany, Italy
The San Quirico Cypresses PC: Shutterstock | Barat Roland

Guided Tours from Siena or Florence to the Val d’ Orcia

From Siena, you can do this highly rated small group tour that will take you to Pienza, Montalcino, and Montepulciano. The price includes tastings of local wines and foods, and visits to wineries.

Book this Val d’ Orcia tour from Siena now!

From Florence, you can check out this well-reviewed cheese and wine tour of Pienza, Montepulciano, and Montalcino! Included in the tour price are two wine tastings and a sampling of the local pecorino cheese.

Book this Val d’ Orcia full day tour from Florence now!

More Information for Your Tuscany Trip

Planning a visit to Tuscany? Be sure to read our article on the top things to add to your Tuscany bucket list.

Check out our in-depth 7-day Tuscany itinerary, which covers the must-see places in Tuscany for first-timers, including Florence, Siena, Pisa and Lucca, San Gimignano, and, of course, the Val d’Orcia.

Also discover how to spend one perfect day in Siena, and check out the top ten things to do in Florence on your first visit!


Venice: How to Spend Two Perfect Days in Venice
Amalfi Coast: Driving Italy’s spectacular Amalfi Coast
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

Did you find this article informative? Pin it for later reference!

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

Like this article? Share it with your friends!


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.

14 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.

      • This is really helpful. We are staying in cerreto guidi and I wasn’t sure about the timing of this drive and how much I would be able to see. Now I feel better! I think with your guide I will be able to see plenty! Thank you!

  5. Hi, we are visiting Pienza next week and we would like to go to Montepulciano for a few hours in the evening. Is it possible to drive through the Val d’Orcia on our way to Montepulciano? or do we have to do a separate drive? also, on Sunday we have a full day available, do you suggest going to Florence or some place else? thank you and well done on your posts!

    • Hi Yanika! To suggest a route, it would help to know from where you are driving to Pienza, but yes, you can include Montepulciano in the same drive. You can do a loop from Pienza to San Quirico d’Orcia, then to Monticchiello and on to Montepulciano.
      Florence is always a great idea, but of course, you would need to pick and choose what to do, since there is so much to see and do there. Siena is smaller and another wonderful destination in Tuscany: the duomo there is one of my favorites.

  6. How much time did you spend in each town? With a total drive of close to 4 hours, I can’t figure out how to fit everything in. 1 hour in each place? (That’s 12 hours, not including dinner and lunch) Is one hour enough for Montepulciano? Parking and waking up to each town also takes time…

    • About an hour in each of the three major towns, and about 30 minutes at each of the abbeys. It is a long day, I agree. If you want a more relaxed pace, you can always skip some of the stops.


Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.