Discover the most beautiful stops in Val d’Orcia, Tuscany. This slow-travel road trip itinerary takes you from through cypress-lined roads and dreamy hilltop towns. We based ourselves at Relais della Rovere in Colle di Val d’Elsa and spent our days exploring the small towns, chapels and scenic drives that make Val d’Orcia one of the most photogenic corners of Tuscany.
1. Podere Baccoleno – The Iconic Winding Road
You’ve probably seen this view hundreds of times online, but it still has the power to make you fall in love with Tuscany. There is no official parking lot here, but a small gravel area along the roadside fits about three to four cars. Park carefully, walk a few metres and you’ll find the classic angle. It’s a popular spot, so expect to see other travellers taking photos and videos too.
2. Cypress Circle near San Quirico d’Orcia
A perfectly round cluster of cypresses sits in an open field and is often overlooked by travellers. It is right off the main road SR2, which makes it an easy stop for a quick photo or video before moving on. There is no official parking area, but you can usually find a small space nearby to pull over safely.
3. San Quirico d’Orcia and the Horti Leonini Gardens
A lovely pause on your Val d’Orcia drive and one of the most peaceful towns in the area. We stopped here for lunch at La Bottega di Ines, a cosy spot with simple, local dishes. After lunch take a slow walk through the Horti Leonini gardens, a 16th-century Italian garden right in the centre of town, and enjoy the quiet atmosphere before continuing your trip.
4. Pienza
The Renaissance jewel of Val d’Orcia, famous for pecorino cheese and panoramic terraces. Every street here feels like a perfect photo spot. Wander the narrow streets, pop into little food shops and enjoy the views over the valley. It’s my favourite stop on this route. I recommend arriving in the morning or evening when the light is soft and the streets are quieter. We parked at Parcheggio Via degli Archi, a paid parking lot just outside the historic centre. You pay at the parking meter/ticket machine. Rates when we visited were about €1.70 per hour, €6 for five hours or €12 for 14 hours. From the lot it’s only a short walk into town.
For more tips on what to see and do in Pienza, read my post about it here[insert link].
5. Gladiator Road
This unpaved lane between Pienza and the Vitaleta chapel was the filming location for the wheat-field scenes in Gladiator. It’s one of those spots that instantly feels cinematic, with rolling hills and tall cypresses framing the track. Park in the small lot near the start of the road or pull over carefully on the side, then walk down the street to get the best view. Visit in the early morning or at sunset for the softest light. On the way you also will find a small beautiful church.
6. Cappella della Madonna di Vitaleta
A tiny stone chapel standing alone in the fields between San Quirico d’Orcia and Pienza. It looks almost unreal in photos, but it truly sits there in complete silence surrounded by rolling hills.
You reach it from the SP146 road. Look for a small sign that points that points to a white gravel road. Follow that road for about 2 km, then park your car at the small gravel space. From there it’s an easy 500-metre walk to the viewpoint.
We arrived in the afternoon, hoping to stay there longer and catch that magical golden-hour light for photos. The area was being prepared for a wedding, so we couldn’t get those sunset shots, but the atmosphere was still beautiful and calm. There’s a small terrace next to the chapel where you can buy drinks and sit facing the view of the valley.
7. Pallazo Massaini
Palazzo Massaini sits right in the heart of Val d’Orcia, surrounded by vineyards and olive trees. It’s now used as a wine estate and accommodation, but even if you are not staying there you can still stop for the view. There is space to park along the main road, then you can walk down the cypress-lined gravel path that leads towards the estate. The scenery opens beautifully on both sides, especially in the late afternoon, and it’s one of those quiet spots where you can just stand and take in how peaceful Tuscany really is.
Exploring Val d’Orcia by car is not just about ticking off locations. It’s about slowing down, stopping whenever a view catches your eye and collecting small moments between one stop and the next. Whether you follow my exact route or just pick one or two places from this list, I promise the valley will stay with you long after you leave.
