Easily one of the most picturesque regions you’ll ever explore, Val d’Orcia is like something out of a dream.
Imagine driving through rolling green hills, golden fields stretching to the horizon, and winding roads lined with perfectly placed cypress trees—that’s Val d’Orcia, the dreamy heart of Tuscany.
Nestled in the province of Siena, this UNESCO-listed region is home to some of the most breathtaking landscapes in Italy, not to mention some seriously charming medieval towns. If you’ve ever daydreamed about sipping wine in a sun-drenched vineyard or strolling through a postcard-perfect village, this is the place to make it happen.
Val d’Orcia is where you’ll find iconic spots like Pienza, Montalcino, and Montepulciano, each offering its own mix of history, culture, and delicious food.
Think world-class wines (hello, Brunello di Montalcino and Vino Nobile di Montepulciano!), fresh Pecorino cheese, and rustic trattorias serving up the best homemade pasta.
From exploring medieval streets in Montepulciano to staying in a fairytale farmhouse to soaking in natural hot springs, we spent the most amazing six days exploring the region.
Ready to start planning your own ultimate Tuscan road trip?
Here’s the perfect Val d’Orcia itinerary!
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Renting a Car in Italy
First things first, you’re going to need a rental car or a private driving service to do this trip.
Driving here is great because of the open roads, but once you hit the smaller towns, parking can be a real headache.
My tip? Arrive early so you can grab a spot before the crowds show up. San Gimignano, for example, can be a parking nightmare with all the tour buses around.
Most rental cars in Europe are manual, so if you prefer an automatic, be sure to book that in advance.
And just a heads-up: driving in Florence is the absolute worst, so if that’s your starting point, be prepared. You might also consider flying in and out of Rome instead to start your trip.
Overall, the prices are pretty reasonable, so renting a car is a solid option for getting around.
Where to Stay in the Val d’Orcia
Depending on the size of your travel party, the region offers endless accommodations, from quaint agriturismos to sprawling villas. My recommendation is to base yourself in one spot and then take day trips to different villages and destinations in the Val d’Orcia.
We traveled as three adults and a baby and decided to base ourselves in Montepulciano.
My family and I booked Casanova dei Boschi through Vrbo—it was a fairytale villa come true! We enjoyed slow mornings in the garden, booked a cooking class with a private chef through the owner, and enjoyed wine by the fire each night.
This farmhouse is perfect for friends or family. It has five cozy bedrooms, a full kitchen, a living room, and a wood-burning fireplace, so you’ll feel right at home.
Located just a 10-minute drive from the hilltop village of Montepulciano, this central location is convenient yet still allows you to immerse yourself fully in the countryside.
Check out some other amazing villas in the Val d’Orcia region here!
Staying at Casanova dei Boschi: An 18th Century Farmhouse in Tuscany
We recently spent 5 nights at the enchanting Casanova dei Boschi, an 18th-century farmhouse in the heart of the Val d'Orcia in Tuscany.
Read More!Staying at an Agriturismo in the Val d’Orcia
If you want to experience the magic of Val d’Orcia, staying at an agriturismo is the way to do it. These charming, family-run farm stays give you a front-row seat to Tuscany’s stunning countryside—think rolling vineyards, olive groves, and golden wheat fields right outside your window.
Unlike a typical hotel, agriturismos offer a more authentic, slow-living experience. You can wake up to homemade breakfasts with fresh-baked bread and local honey, sip wine produced on-site, and even try your hand at traditional Tuscan cooking.
Whether you’re looking for a rustic farmhouse or a luxe estate with an infinity pool overlooking the hills, there’s an agriturismo for every kind of traveler. Plus, staying on a working farm means supporting local families and sustainable tourism—so it’s a win-win!
Top Hotels & Agriturismos in the Val d’Orcia:
Florence
Day 1:
– Drive from Florence to Montepulciano –
We started our Val d’Orcia road trip from Florence, making our first stop in the charming town of San Gimignano, just an hour away.
This place is pretty popular, so it’s best to arrive early to beat the crowds.
We spent some time wandering around and exploring the fortress, which is super picturesque, so get ready to take loads of photos! Of course, we couldn’t leave without grabbing some ice cream from the world-famous Gelateria Dondoli.
Expect a long queue, but it does move quickly.
I tried their sour cherry and yogurt flavor for a Greek-inspired combo, and it was absolutely DELICIOUS; I would highly recommend it!
After our sweet treat, we continued our drive for another two hours to reach Montepulciano. Once we arrived, we stocked up on essentials at a local grocery store and spent a relaxing evening settling into the villa.
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Day 2:
– Private Driving Tour of Montalcino –
We kicked off day two by hiring a private driver to explore Montalcino (so that we could safely taste as much wine as we wanted), but you could also self-drive each day!
Our first stop was Biofattoria L’Upupa, where we enjoyed a wonderful lunch and toured their agriturismo. In case you missed it, an agriturismo is a working farm offering accommodations and meals. Even if you don’t stay at one, you can visit some for a meal.
They’re lovely to support because they keep small farms in operation, giving you an authentic taste of rural Italian life.
After our meal, we went on a wine tour and tasting at Tenuta Fanti. Their wines were top-notch, and the tour gave us great insight into regional winemaking.
Expedia Tours & Day Trips
Did you know you could book day tours and activities through Expedia? Discover a world of unforgettable experiences with tours and day trips on Expedia!
Plus, you can earn and spend ‘OneKeyCash’ (Expedia Group’s rewards currency) on cozy Hotels.com stays, awesome Vrbo vacation rentals, and even more on Expedia.
You can rack up OneKey rewards on eligible bookings for everything related to your travel escapades. We’re talking about hotel stays, car rentals, activities that make your heart race, cozy home rentals, and even flights that take you to new horizons.
You can sign up for free to earn and save for that next trip!
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Day 3:
– Explore Montepulciano –
This hilltop town, with its stunning medieval charm and gorgeous views, is one of my favorite spots in Val d’Orcia!
Our first stop was Caffe Poliziano, where I highly recommend grabbing a seat on the balcony to enjoy your morning coffee. If the balcony is full, don’t worry—the interior is equally beautiful!
For lunch, we stopped at Bistrot Del Tribunale. While the Pistachio pizza was good, the service was majorly disappointing, so I wouldn’t actually recommend this spot. Instead, next time, I’d try Osteria del Borgo or La Vineria di Montepulciano.
After wandering around the town’s nooks and crannies, we stopped in at Cantine Contucci for some wine tasting and shopping, picking up a few bottles to enjoy by the fire later. Our afternoon in the town ended at Piazza Grande, followed by a scenic walk to the Veduta Panoramica for insane panoramic views.
Our Vrbo host helped arrange a cooking experience with an in-house chef in the evening!
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Day 4:
– Visit Fosso Bianco in Bagni San Filippo –
Initially, we had planned to make the 5-hour round trip to Saturnia hot springs (the ones you’ve probably seen all over Instagram). But a few people suggested it wasn’t worth the trip.
I was told that the way is not that hot, it’s often overcrowded, and there are weird red worms in the water.
Instead, I was recommended to visit Fosso Bianco in Bagni San Filippo, only 45 minutes away.
We had an amazing experience—I’d 10/10 recommend it!
This natural thermal wonderland has stunning white mineral formations that are so much fun to explore. The small pools seemed to get warmer the higher we went.
NOTE: Get there early to get a decent parking spot. Getting to the hot springs is a bit of a trek, so plan accordingly. And don’t forget to pack towels and a change of clothes.
Day 5:
– Visit Pienza –
Pienza is another charming hilltop town renowned for its delicious pecorino cheese.
We began our afternoon visit by stopping at La Taverna del Pecorino for cheese tasting and shopping. Next, we enjoyed a wine experience at Enoteca di Ghino, a beautiful setting in the center of Pienza.
We dined at Trattoria Latte di Luna for lunch and devoured some truffle pasta and toast with pecorino and truffle honey. Another great option for homestyle Italian meals is Sette Di Vino.
To sweeten the day, we grabbed gelato at Fredo before wandering through the Palazzo Piccolomini garden, soaking in the gorgeous views.
Now, that’s what I call a day of indulgence!
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Day 6:
– Montepulciano to Siena to Florence –
We dedicated our last day to exploring Siena, a city that’s both huge and absolutely incredible. Plan for a full day in Siena; there is so much to see!
Be prepared for a lot of hills, so make sure to wear comfortable shoes!
We started with a visit to the stunning Siena Cathedral. DON’T MISS this or the breathtaking panorama from the unfinished nave of the “New Cathedral.”
In 1348, the plague killed more than half of Siena’s population, so the cathedral was never finished.
One of the best things to do in Siena is to get lost in the maze of streets around Piazza del Campo. We loved wandering the city streets and discovering smaller squares, small churches, cafes, shops, and restaurants. Stop by Via di Città, one of the main streets perfect for shopping.
Another highlight worth visiting is Santa Maria della Scala, one of Europe’s first hospitals.
After soaking in Siena’s charm, we drove an hour back to Florence to catch our flight, wrapping up an unforgettable Tuscan adventure.
Feeling inspired by this 6-day Val d’Orcia itinerary?
Keep on planning your dream Italian escape with my Ultimate Two-Week Italy Itinerary!
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