Agriturismo Baccoleno
Located near Asciano, Agriturismo Baccoleno is one of Tuscany’s most iconic photo spots. The winding cypress-lined driveway looks like something straight out of a movie and offers a dreamy view, especially during golden hour. It’s one of those places where you’ll want to stop and admire the sheer beauty of the landscape before reaching for your camera.
Keep in mind, this spot can get quite crowded during sunset as many professional photographers gather here to capture the perfect shot.
Here is the exact location. You can park on the side of the road for a short time—just be careful, as space is limited!
Cypress Trees at Monticchiello
Monticchiello is a charming medieval village, but it’s the winding, cypress-lined road just outside the town that draws photographers from all over. The curving road, framed by green or golden fields depending on the season, is the perfect spot for that quintessential Tuscany photo—especially during sunrise or sunset when the light is soft and magical.
You can find the road here, but for a perfect view of the curves from a distance, head to this spot.
Chapel of the Madonna di Vitaleta
The Chapel of the Madonna di Vitaleta is a tiny, picturesque chapel nestled between two cypress trees on a hill, offering mesmerizing views of the Val d’Orcia countryside. It looks like it’s straight out of a painting, making it a dream location for photographers. While it’s popular later in the day, sunrise here is surprisingly peaceful, with only a few local photographers around. We visited it during sunrise, and it was just us and another photographer there.
The sun rises directly behind the chapel, giving you that perfect postcard shot.
Here is the exact location of the photo spot. To reach it, park around here, as the road is closed off with a fence, and then take a short 10-minute walk to the chapel.
Be mindful, though, as there’s a private property nearby, so respect the space while capturing your perfect shot.
Cypress Trees of San Quirico d’Orcia
Just outside the town of San Quirico d’Orcia, you’ll find one of the most photographed spots in the world—the famous cypress trees. These iconic trees, standing proudly on small, isolated hills, are a symbol of Tuscany, and especially characteristic of Val d’Orcia.
There are two distinct groups of trees: the first group of cypresses is located here, and the second group, the Cypress Ring, is just down the dirt road here.
No matter the season, the landscape changes around them, but the cypress trees remain timelessly beautiful, always creating the perfect photo backdrop.
La Foce Cypress Road
For that classic winding road lined with cypress trees, head to La Foce, located between Chianciano Terme and Montepulciano. This curvy road twists through the rolling hills and is one of the most iconic spots to capture Tuscany’s landscape. The best photos are taken from a slight elevation, so you can really see the full shape of the road.
Here is the exact location of the road if you want to drive it, but for the best view, head to this viewpoint.
Gladiator Shooting Spot
Just outside Pienza, there’s a hidden gem for movie fans, especially if you’ve watched Gladiator countless times! This spot, located here, is where some of the famous scenes were filmed. The landscape and views are typical of Tuscany, but knowing the cinematic history behind it makes this place truly special.
Park by the church (parking is limited) and walk down the dirt track—it’s about a 10-minute walk. Once you reach the bottom, follow the small paths to the right side of the hill to line up with the best vantage point. The climb back is steep, so be prepared for a little workout!
Pienza: Overlook the Val d’Orcia Valley
Pienza is known for its breathtaking views over the Val d’Orcia valley, making it a perfect photo spot. The panoramic vistas from the town’s edges, especially around Via dell’Amore, provide wide-open views of the rolling hills and cypress trees.
The lighting here is beautiful at any time of day, but early morning or late afternoon gives you that perfect soft light.
Also, here is a bonus spot right next to Pienza, that is pure Tuscany!
Viale di Cipressi
Viale di Cipressi, located near Pienza in the heart of Val d’Orcia, is one of Tuscany’s most iconic landscapes. This picturesque cypress-lined road winds through rolling hills and leads to Podere Baccoleno. It’s famous not only for its stunning beauty but also for being a real representation of Tuscany’s rural charm. Photographers and travelers alike gather here to capture the lines of cypress trees, especially during golden hour, making it one of the most Instagrammable spots in the region.
Here is the location, you can park there for a few minutes because this is a private road, so be mindful.
Final Tip: Don’t miss Sunrise or Sunset!
The real magic of Val d’Orcia happens during the golden hours—just after sunrise and just before sunset. That soft, golden light really brings out the beauty of the landscape and sets up the perfect conditions for photography.
I know, it’s hard to wake up early on vacation, but trust me—it’s so worth it. When we were exploring Tuscany, our daily routine was simple: wake up at 5 AM, hit the photo spots, explore, grab breakfast, take a nap, explore some more until sunset, dinner, sleep, and repeat. It’s a routine that paid off with some of the best photos we’ve ever taken!
If you’re looking for more spots to explore and capture, check out our blog Best Things to Do in Val d’Orcia. Until next time, be mesmerized! 🧡