In a nutshell
- The Orcia Valley sits in the southeast of Tuscany and is a UNESCO World Heritage Site — this is where Tuscany’s most iconic landscapes come from.
- It’s known for breathtaking viewpoints, scenic roads, cypress-lined avenues, and small medieval villages like Pienza and Montalcino.
- The highlights of the Val d’Orcia are spread across the landscape, so we’ve put together a well-planned 3-day route that hits all the must-sees without the guesswork.
- A stay at a winery or agriturismo is part of the experience — you’ll find our specific accommodation picks right in the article.
What is the Val d’Orcia?
The Val d’Orcia, or Orcia Valley, is a landscape in the southeast of Tuscany, about a two-hour drive from Florence. It’s a UNESCO World Heritage Site.
This is where the iconic postcard images of Tuscany come from: rolling hills, scenic roads, breathtaking sunsets, and solitary farmhouses — you can probably picture them right now.
Plan at least two to three days to take in all the highlights of the Val d’Orcia.
Your Val d’Orcia Route on a Map
We’ve mapped out our personal route to the most beautiful sights in the Val d’Orcia for you. This gives you a rough overview of what’s where.
We’ve put together the best Val d’Orcia road trip itinerary for you. It covers all the major highlights of the area and takes three days, with two overnight stays — accommodation tips included.
To fit everything into your daily schedule, start your Val d’Orcia tour as early in the morning as possible, since the drive from Florence or Siena takes one to two hours.
Montalcino
Montalcino is your first stop on our Val d’Orcia road trip.
The small town sits on a hill and, with its sweeping views, is considered the gateway to the Val d’Orcia. A perfect starting point for exploring the valley!
Set aside one to two hours for Montalcino — even though the town is small, there’s a lot to see.
Medieval palaces, a cathedral, a fortress, city walls, and centuries-old wine cellars — this is where Italy’s most famous wine is produced: the Brunello di Montalcino.
You can taste it pretty much everywhere in town, or go on a guided wine cellar tour:
Book a wine cellar tour in Montalcino
Cypress Trees of San Quirico d'Orcia
From Montalcino, head toward San Quirico d’Orcia, another small but seriously charming village in the Val d’Orcia.
Along the way, you’ll pass a spot that’s especially popular with photographers: a small cypress grove sitting right in the middle of a field near San Quirico d’Orcia. It’s right along country road SR 2 toward San Quirico d’Orcia.
The spot has something almost mystical about it and draws photographers at all hours of the day and night — so don’t expect to have it to yourself.
Carry on down the country road and you’ll reach San Quirico d’Orcia in about ten minutes. Plan one to two hours here for sightseeing.
San Quirico d'Orcia
Even though San Quirico is small, it held real importance in the Middle Ages. It lies along the pilgrim route Via Francigena (the Frankish Road), which runs from England all the way to Rome.
That history shows in the sheer number of remarkable structures packed into this little village: a city wall with 14 towers, a medieval church, an ornate town hall, a public Renaissance garden, and plenty of small lanes lined with artisan boutiques and trattorias.
Our lunch tip in San Quirico d’Orcia: Ristorante al Vecchio Forno, with a lovely garden for outdoor dining.
Podere Belvedere
From San Quirico, continue on to Pienza — which also makes the best base for your first overnight stay in the Val d’Orcia. But there are a few stops along the way that are especially stunning in the late afternoon.
The first is the classic photo spot of Tuscany — and you’ve almost certainly seen this image before: a farmhouse with a red tile roof set among rolling hills, surrounded by cypress trees.
The house is called Podere Belvedere and sits right in the heart of the Val d’Orcia. The viewpoint where you can take it all in is along the scenic road SP146, which runs from San Quirico to Pienza.
Note: The house is further from the road than it looks in photos. If you’re a photographer, bring a telephoto lens.
Cappella Madonna di Vitaleta
Another great vantage point is just a few minutes further down the road toward Pienza.
From the roadside, you look out over the solitary Cappella Madonna di Vitaleta — another classic postcard image of Tuscany.
You can’t really miss the spot, since there are always plenty of other visitors’ cars parked here.
The chapel stands in the middle of a field, surrounded by cypress trees with Monte Amiata in the background.
If you’re here at sunset, the reddish light shines directly onto the chapel and you can get some truly stunning shots. It’s also not as close to the road as it appears — so pack a telephoto lens!
Pienza
Pienza sits on a hill in the heart of the Val d’Orcia, and the walking path that circles the entire village offers a seriously stunning panorama of the landscape.
Pienza is full of small, winding lanes, and features a cathedral, observation terraces, and plenty of boutiques where you can pick up the typical local delicacies of the Val d’Orcia.
Don’t leave without trying the Pecorino di Pienza, one of the most celebrated cheeses in all of Italy!
Our restaurant tip for dinner in Pienza: Trattoria Buca delle Fate, set in a gorgeous vaulted cellar from the 15th century.
Overnight Stay in Pienza
If you’re on a road trip through the Val d’Orcia, staying at a typical Tuscan agriturismo is simply part of the experience. These are wineries or farms that also offer accommodation.
A really lovely option is the Borgo Sant’Ambrogio, about five minutes outside of Pienza, with an infinity pool, beautiful garden grounds, and a classic Tuscan restaurant. It’s well-kept and genuinely comfortable — which is worth its weight in gold after a full day of sightseeing. It’s easily one of our top hotel picks in Tuscany.
Check availability at Borgo Sant’Ambrogio
Gladiator Filming Location
On day two, you’ll leave Pienza and head toward Monticchiello and Montepulciano.
This stretch has some stops you really shouldn’t skip — including the Strada di Terrapille trail, which will be instantly recognizable to anyone who’s seen the film Gladiator.
Throughout the film, the main character Russell Crowe’s longed-for home appears repeatedly, meant to represent his house in his homeland of Spain — but it was actually filmed right here in the Val d’Orcia.
The iconic view from the film is visible along a gravel road that branches off from the main road.
There’s a small parking lot here, so you can leave the car and continue along the unpaved path on foot.
The path winds through fields past scattered cypress trees — pure Tuscany. Honestly, it’s worth the walk even if you’ve never seen the movie, because the landscape is simply stunning.
Monticchiello
After walking back to the car, the route continues to Monticchiello, a tiny village perched on a hilltop in the Val d’Orcia.
Along the way you’ll pass some breathtaking views — the most famous being a zigzag panoramic road lined with cypress trees.
The best vantage point is from an unpaved country lane that branches off the SP88. You can find the exact spot on Google Maps.
Monticchiello itself is truly tiny — you can see everything in about an hour. Still, the stop is totally worth it, because the village is far less crowded than Pienza or San Quirico d’Orcia.
Outside the city walls there’s a free parking lot. From there, walk through the town gate into the village on foot.
Fun fact: despite its tiny size, Monticchiello is home to the acclaimed Ristorante Daria, which holds a Michelin star. We’d point you toward the Osteria La Porta, though — it has an outdoor terrace with a wonderful view!
Montepulciano
From Monticchiello, it’s about 15 minutes to Montepulciano. On the drive, you can already spot the town from a distance, perched dramatically on a steep hill above the Val d’Orcia.
Plan a few hours for Montepulciano — there’s genuinely a lot to take in.
The heart of the town is the central square, Piazza Grande, surrounded by historic palaces.
This is also where you’ll find the Palazzo Comunale with its bell tower, which you can climb. It’s absolutely worth it — the vista over the entire Orcia Valley is really impressive.
Wander through Montepulciano’s medieval lanes and pop into one of the historic wine cellars to taste the town’s most celebrated export, the Vino Nobile.
Our restaurant tip in Montepulciano: Cantina Gattavecchi, with a wine cellar dating back to the 12th century and a fantastic panoramic terrace.
Overnight Stay in Montepulciano
After a packed day, we recommend staying right in the historic center of Montepulciano. That way you don’t have to drive anywhere after sightseeing and dinner.
The Dimora Dell’Erbe Rooms offers great value for the money. The bed & breakfast has six individually decorated rooms, all located right in Montepulciano’s historic center.
Check availability at Dimora Dell’Erbe Rooms
Cypress Avenue of Poggio Covili
After breakfast in Montepulciano, continue toward Bagno Vignoni.
To get there, you’ll cross the entire Val d’Orcia again, since the two towns sit on opposite sides of the valley. The drive takes about half an hour.
Just before Bagno Vignoni, make one more stop at another classic Tuscan photo spot: the perfectly straight cypress avenue of the Poggio Covili farmhouse. The entrance is right along country road SR2 toward San Quirico d’Orcia.
The avenue is private, so you can’t walk along it. But you’re absolutely welcome to take selfies in front of the entrance — it’s the perfect shot for your Instagram feed!
Bagno Vignoni
Bagno Vignoni is a tiny village that grew up around hot thermal springs more than 2,000 years ago.
One of those springs lies beneath the main square and feeds the enormous thermal pool with water heated to 49°C (120°F).
Swimming in the pool itself is off limits, but to the left of the piazza a small path leads to the public bathing spots in the Parco dei Mulini. Here you can bathe for free in several naturally formed pools — though there are no showers or restrooms.
If you’re after a proper wellness day, there are dedicated thermal spas in Bagno Vignoni for exactly that — for example at the Le Terme Wellness & Spa center.
Lies auch:
Agriturismo Baccoleno
To wrap up your Val d’Orcia road trip in style, make one final stop at another famous photo spot: the cypress avenue of the Agriturismo Baccoleno. Conveniently, it’s right on the way back to Siena or Florence.
From Bagno Vignoni it takes about 40 minutes, and if you time your arrival for sunset, you can take some truly beautiful photos.
The viewpoint is along the country road Strada Provinciale del Pecorile. You can’t miss it — especially at sunset, there are always cars parked here.
From the road, a path leads up the hill to the best view of the winding cypress avenue.
You can get great shots here with your smartphone too — no telephoto lens needed.
And that’s your last stop on our Val d’Orcia itinerary. From here, you’re about 50 minutes from Siena or 1.5 hours from Florence.
The Most Beautiful Wineries to Stay at in the Val d’Orcia
Staying at a Tuscan winery is simply part of the Val d’Orcia experience. We’ve already covered two great places to stay that fit perfectly into our route.
But if you want to extend your time in the Val d’Orcia, here are three more agriturismi that offer outstanding value for the money:
Lies auch:
Extra Tip: Swimming at the Coast
The coast is only about 2–2.5 hours by car from the Val d’Orcia. So you can easily tack on a few beach days to your trip.
There are some truly beautiful beaches in Tuscany. We especially recommend the beaches around Castiglione della Pescaia — they pair really well with a Val d’Orcia road trip. Here are the best ones:
- Cala Violina: a little off the beaten path, with golden sand and turquoise water. You’ll need to book your visit in advance on the official website.
- Follonica: miles of sandy beach with excellent facilities
