Top Things to Do in Val d’Orcia

Val d’Orcia represents everything you imagine when you think of Tuscany—rolling hills, cypress-lined roads, medieval hilltop towns, and sprawling vineyards. This UNESCO World Heritage site is a paradise for anyone looking to explore the heart of Tuscany. Incredible views, amazing food, and roads that ldrive through postcard-perfect landscapes, Val d’Orcia is a perfect place to explore! We’ve been lucky enough to visit Val d’Orcia several times, and on each trip we discover something new. So here are our top recommendations for making the most of your time in this beautiful region! (P.S. we will also share some personal favourites restaurants!)

Pienza: The Perfect Postcard Town

When you picture Tuscany, you’re likely picturing Pienza. This charming town sits perfectly perched on a hill and offers sweeping views over the Val d’Orcia valley. It’s no wonder Pienza was designed as the “ideal Renaissance town” by Pope Pius II. Every street, square, and building looks like it belongs on a postcard.

Aside from its beauty, Pienza is also the home of the famous pecorino cheese. If you’re a cheese lover, don’t miss out on visiting a local cheese shop or, even better, taking a pecorino-making tour. We also had one of our best meals here at Trattoria Latte di Luna. The family-owned restaurant serves simple but incredibly delicious food—Nonna still cooks there, and yes, they really do pick the basil straight from their garden, it’s that fresh!

Tip: Pienza has some cute small shops where you can buy souvenirs, but the best souvenir we ever brought back home was pecorino cheese!

Pienza: Dairy Farm Tour with Pecorino Cheese Tasting

Visit a dairy farm in the hills of Val d’Orcia to observe the techniques of cheesemaking.

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San Quirico d’Orcia: Hidden Gem of Tuscany

Often overlooked, San Quirico d’Orcia is a little gem tucked away in the heart of the region. Its medieval streets and stone buildings give you that authentic, off-the-beaten-path experience. One of the highlights here is the Horti Leonini, a perfectly manicured Renaissance garden that’s a great spot for a quiet walk or just taking in the atmosphere.

San Quirico is also home to one of the most iconic views of the Tuscan countryside—those famous cypress trees lined up on a hill. You’ll find this scene right outside the town, and trust us, it’s as breathtaking in person as it is in the photos.

Tip: If you’re a foodie like us, San Quirico has several restaurants in the Michelin Guide. We went back two nights in a row to a local favorite—Trattoria Osenna—because, well, the food was just that good!

Montepulciano: A Taste of Tuscany’s Best Wines

Famous for its Vino Nobile di Montepulciano, this medieval hilltop town is a must-visit for wine lovers. As you wind your way uphill through Montepulciano’s cobbled streets, you’ll pass by wine shops, charming cafes, and artisan stores. Piazza Grande, the town’s main square, is surrounded by beautiful Renaissance palaces and offers incredible views over the Val d’Orcia and Val di Chiana.

Montepulciano also has a bit of a cinematic side—movies like Under the Tuscan Sun and The Twilight Saga: New Moonwere filmed here. So if you’re a fan, you might recognize some spots from the big screen!

Tip: a few minutes from Montepulciano we had an amazing dinner in La Cacina, the owners were lovely and the food was perfect with a bit of twist. They also make their own olive oil which we tasted during dinner, and we ended up buying the olive oil for the whole family back home.

Explore the Val d’Orcia and Chase That Sunset!

Driving through Val d’Orcia isn’t just about getting from point A to point B—it’s about enjoying the beauty around every corner. The winding roads take you through some of Tuscany’s most iconic landscapes, with rolling hills, golden fields, and those picture-perfect cypress trees. You’ll find yourself pulling over more times than you can count to snap photos of the incredible views.

One of the best drives is along the SR2, passing through Pienza, San Quirico d’Orcia, and Bagno Vignoni. But the real magic happens as the sun starts to set—the golden light that bathes the hills makes the scenery even more breathtaking.

Tip: For the best experience, time your drive for early morning or late afternoon. Sunset in Val d’Orcia is truly unforgettable, and trust us, you’ll want to chase that light all the way to your next stop!

If you’re looking for photo spots, we got you covered – Tuscany’s Hidden Gems: Best Photo Spots for Photographers

Val d’Orcia is more than just a pretty face—it’s a place where every turn offers something new to discover, whether it’s a cozy village, a scenic drive, or a bowl of the best pasta you’ve ever had. If you’re planning a road trip through Tuscany, this region is one you can’t miss. And if you’re anything like us, once you’ve been, you’ll find yourself returning year after year.

If you want to explore more of Tuscany, be sure to check out our other guides:

Until next time, be mesmerized! 🧡