Best Towns in Val d’Orcia You Can’t Miss on Your Tuscany Trip
There are so many romantic and cozy movies that are set in Tuscany, where the filming environment becomes part of the story. This Italian region has a unique charm, and there are many details that contribute to its dreamy, romantic atmosphere.
One of my favorite places in Tuscany is Val d’Orcia, a region that truly feels like the heart and soul of the area. I’m dedicating this article as a Val d’Orcia travel guide, focusing on one of the most important parts of its charm: the beautiful and glorious towns and villages.
At first glance, the towns of Val d’Orcia Tuscany may seem small, but together they embody the very essence of Tuscany. If you’ve traveled through Europe, chances are you’ve already seen many medieval villages that look quite similar, with cobblestone streets, old churches, and citadels.
I have seen a lot of medieval landmarks, so it was hard to find something that truly stood out—at least until I visited Val d’Orcia. Here, the combination of timeless beauty, authenticity, and atmosphere makes the region feel special and unforgettable.
In Val d’Orcia, every town has its own personality. Some feel elegant and refined, others rustic and raw, while a few give the impression of hidden gems, secrets kept only for those who wander a little further.
I vividly remember that, even though we explored many medieval towns in Val d’Orcia in just three days, I could clearly distinguish each one. Even with their similarities and medieval heritage, each place had something specific that made it unique.
As I mentioned, all the towns shared the same backdrop of rolling hills, cypress-lined roads, and that sense that life moves slower and more meaningfully here (along with the constant challenge of finding any kind of parking—free or paid—but that’s a story for another day :)).
This is why a Val d’Orcia itinerary is perfect if you are looking for a slow travel destination.
Now, let’s explore together the best towns in Val d’Orcia!
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Table of Contents
Why Visit the Towns of Val d’Orcia
Why visit the best towns in Val d’Orcia, you may ask? Well, if my long introduction at the beginning of this article didn’t convince you, then let me share the reasons again in a shorter and easier-to-read version:
- The medieval charm. I don’t know about you, but for me, medieval towns always have a unique beauty and a romantic vibe. Add to this the authentic Italian atmosphere, and you’re sure to be charmed.
- Postcard landscapes. Some landscapes look like a dream—like something you only see in paintings or photos. Well, these places truly exist in Val d’Orcia Tuscany, and in Tuscany in general.
- Authentic Tuscan life. People in Val d’Orcia have built a culture around their famous wines, cellars, and traditional food recipes. They seem to have discovered the best way to live and enjoy life, making Val d’Orcia food and wine experiences unforgettable.
- A slow travel destination. If you are looking for a vacation where you can relax, slow down, enjoy delicious food, and drink world-class wine while spending your time watching people or admiring charming landscapes, then this Val d’Orcia travel guide points you to the perfect destination.
Pienza – The City of Pecorino Cheese
Renaissance architecture and UNESCO heritage
When I think about Pienza, I remember the good food, the narrow streets, the hidden hillside views, and how every detail felt so harmonious. Since it was designed as the “Ideal Renaissance City” by Pope Pius II, walking through its streets you’ll notice that everything feels more refined: the piazza opens up in perfect proportions, and the buildings reflect a sense of balance.
The central square, Piazza Pio II, with its cathedral, papal palace, and town hall, is a true masterpiece of Renaissance urban planning – and today it’s recognized as part of the UNESCO World Heritage Sites, making it a must-see stop on any Val d’Orcia itinerary.
Things to see and do in Pienza
If you want to capture the full essence and beauty of Pienza, you don’t necessarily need a strict itinerary or checklist—you only have to walk around and explore at your own pace.
But if you have limited time and want to make sure you see every important landmark—or if you enjoy checking things off a list—here are the main highlights you shouldn’t miss while in Pienza:
- Piazza Pio II. The heart of the town and a UNESCO World Heritage Site. Around it you’ll find the Cathedral (Duomo di Pienza), Palazzo Piccolomini, and Palazzo Comunale.
- The Diocesan Museum (Museo Diocesano). Home to Renaissance paintings and religious artifacts.
- Church of San Francesco. A small Gothic church with frescoes still intact.
- Local artisan shops. Here you can discover cheese, ceramics, olive oil, and other handmade Tuscan crafts.
Pienza is especially famous for its delicious pecorino cheese. For the locals, pecorino is not just food—it’s part of their culture, with traditional recipes passed down through generations. You’ll find many local shops where you can taste different assortments, making this a highlight for anyone interested in Val d’Orcia food and wine.
If you’re looking for an authentic place to eat traditional Tuscan food (beyond pasta), I recommend Sette di Vino. Most of the time it’s fully booked, so you can try making a reservation—or do what we did: wait outside until a table was free. The reviews on Google Maps and TripAdvisor are excellent, and I can confirm they’re well deserved.
The food was simple yet incredibly flavorful, with natural tastes and perfectly balanced portions. We felt like we were dining in the home of a traditional Tuscan family.
This osteria is old-fashioned and located in a quiet square where you can enjoy your meal while people-watching or admiring the cobblestone streets and flower-filled balconies.
Best photo spots in town
If you want to make the most of your visit to Pienza—and capture the beauty for your memories or your own Val d’Orcia travel guide—don’t miss these stunning photo locations:
- Via dell’Amore – a romantic lane with breathtaking views across the valley.
- Via Santa Caterina – the perfect spot to capture sunsets over the rolling hills.
The panoramic terraces along the city walls – where the Tuscan countryside stretches endlessly before you.
Montepulciano – Home of Vino Nobile
Things to do and see Montepulciano
Montepulciano was the first town we visited in Val d’Orcia, and it impressed us for many reasons.
Looking back now, after exploring several other villages in the region, I can say that Montepulciano feels more spacious and grander. Some even compare it to Florence—like a mini-Florence, a countryside version. Even if Montepulciano is bigger, it still feels cozy and remains one of the best towns in Val d’Orcia to explore.
The Renaissance-style buildings, the delicious food, and the world-famous wine make this town an immersive experience in history, tradition, and flavor.
Here’s a list of the best things to do and see in Montepulciano:
- Visit Piazza Grande – the central square surrounded by Palazzo Comunale, the Duomo of Montepulciano (Santa Maria Assunta), Palazzo Contucci, and Palazzo Tarugi.
- Church of San Biagio – located just outside the city walls and surrounded by countryside, this Renaissance masterpiece is a must-see.
- Walk along Il Corso – the town’s main street, lined with chic shops and charming cafés, offering the perfect backdrop for slow wandering and relaxing moments.
- Explore the Medici Fortress (Fortezza Medicea) – where you can learn about wine production and enjoy tastings of Montepulciano’s finest vintages.
- Visit the Torture Museum – small but fascinating, especially if you’re intrigued by dark history. It offers an eye-opening look at medieval interrogation methods and punishments.
- Drink their famous Vino Nobile – the perfect way to slow down and reward yourself after climbing the steep streets of Montepulciano.
- Book a private guided wine cellar tour – where you can enjoy multiple tastings paired with Tuscan snacks, making it an essential experience for any Val d’Orcia food and wine lover.
Best panoramic views
If you’re like me and love discovering amazing panoramic views and perfect spots for photos, then you need to check out these places in Montepulciano:
- Piazza Grande Tower – climb up for sweeping panoramas of the entire Val d’Orcia.
- Via di San Biagio – this spot feels like a real-life painting, with the majestic San Biagio church perfectly framed by rows of cypress trees.
- Panoramic viewpoint in town – this was a hidden location we discovered on Google Maps, without even a specific name. For us, it turned out to be one of the most stunning Val d’Orcia hidden gems, with breathtaking views over the countryside. Check out the exact location on Google Maps below, or head to this address: Vicolo dei Cacciatori, 1, 53045 Montepulciano SI, Italy.
And because you know me—I never gatekeep the best photo spots or viewpoints I discover during my travels—I’m sharing them all here so your own Val d’Orcia travel guide feels even more complete.
Hint: In Montepulciano there are even more panoramic viewpoints, and you can easily find them on Google Maps. They are usually marked with names like “Panoramic view” or “Panoramica Valle.”
- Panoramic view outside Montepulciano. If you have the time and want to make the most of your visit, you should check out this beautiful viewpoint just outside the town. The location is very close—only a 7–10 minute drive from Montepulciano—and it’s worth including in your Val d’Orcia itinerary.
Honestly, I feel like my photos do the best job of showcasing this place, but to make things easier I’ll also leave the address and exact location: 4Q4C+F46 Montepulciano, Province of Siena, Italy.
This kind of short detour is exactly what makes a Tuscany road trip in Val d’Orcia so rewarding—you never know when you’ll stumble upon another breathtaking view. And of course, I had to share it here because no list with the best towns in Val d’Orcia would be complete without it.
Montalcino – The Land of Brunello Wine
The fortress and medieval center
If you go to Montalcino just for its world-famous Brunello wine, you’ll leave with much more: a memorable experience shaped by its raw Tuscan atmosphere.
The Rocca di Montalcino (the Fortress) greets you as you enter the town. You can even climb its walls for amazing panoramic views of vineyards stretching all the way to the horizon.
From there, you can explore the town by walking along narrow alleys, charming small squares, and passing by stone houses that carry a timeless appeal. The streets feel especially authentic, with a strong medieval vibe. I suggest finding a beautiful square, ordering some local food or a cappuccino, and simply immersing yourself in the rhythm of everyday Tuscan life.
We spent only half a day in Montalcino, but I still remember its slow-paced lifestyle and relaxing vibe, much of it tied to its medieval character. For me, Montalcino definitely deserves a place on the list of the best towns in Val d’Orcia, based on its overall atmosphere alone.
Brunello tastings and vineyards
For my husband and me, food is always part of any travel experience. No matter what village or town we visit, we always make time to taste the delicious traditional dishes.
If I had to compare Montalcino with other Val d’Orcia towns (or even Tuscany in general), I would say the food is slightly more expensive and not as diverse.
That being said, you don’t necessarily have to plan your meals here. But if you are a wine lover, I highly recommend trying one of Italy’s most prestigious wines: Brunello di Montalcino.
Many wine shops, called enoteca, will happily offer tastings if you’re interested.
And if you want the ultimate experience, I recommend booking a private wine tasting with an organized tour. It’s the best way to discover the essence of Val d’Orcia food and wine culture while enjoying Brunello in the landscapes where it was born (Private Tour: Montalcino Wine Tasting Experience)
If you are passionate about wine and vineyards in general, then you can also book a Montalcino Castle and Vineyards tour with tasting. This tour will offer you a more authentic experience in the history of wine making, while also tasting a variety of wine aromas.
Things to see in Montalcino
Same as with the other Val d’Orcia towns, you don’t need a checklist to visit Montalcino—just walk around and let yourself be surprised by its beauty. But I also know there are travelers who love having a list, so here are the must-see highlights:
- The Fortress (Rocca di Montalcino) – climb for sweeping views and join a wine tasting inside.
- Museo Civico e Diocesano – featuring medieval art, sculptures, and frescoes.
- Sant’Agostino Church & Cloister – quiet, atmospheric, and perfect for a reflective stop.
- Abbey of Sant’Antimo (just outside town) – a Romanesque abbey surrounded by olive trees and vineyards, only about a 12-minute drive from Montalcino. For me, this place felt peaceful, secluded, and majestic all at once. It’s absolutely worth visiting and remains one of the Val d’Orcia hidden gems.
- Local enotecas – the best way to sample Brunello di Montalcino and compare the work of different producers.
This is exactly why Montalcino deserves its spot among the best towns in Val d’Orcia Tuscany—it combines medieval character with unforgettable food and wine experiences.
San Quirico d’Orcia – A Lesser-Known Gem
Romanesque churches and gardens
San Quirico d’Orcia isn’t as famous as Montepulciano, Pienza, or Montalcino, but in my opinion it’s one of the best towns in Val d’Orcia. For starters, this town is rich in history and architecture.
The Collegiata di San Quirico is a Romanesque church with some Gothic influences and is considered the centerpiece of the town. Another cultural symbol is the Horti Leonini, elegant Renaissance gardens dating back to the 16th century.
Small-town vibe, fewer crowds
Initially, San Quirico d’Orcia wasn’t very high on our Val d’Orcia itinerary when we planned our trip to Tuscany. But we knew we wanted to stay a few nights in Val d’Orcia in a traditional and authentic Tuscan accommodation. We found a beautiful and secluded spot in San Quirico, just outside the town.
I’ll write a detailed review about Agriturismo Bagnaia as part of my Val d’Orcia series. If you want to get notified when I publish more content about this region or Tuscany in general, consider subscribing to my newsletter (no spam or useless emails, I promise).
That being said, because of its proximity to our accommodation, we spent more time exploring San Quirico and were charmed by its small-town vibe. The fewer crowds, quiet streets, and authentic Tuscan atmosphere make San Quirico the perfect stop between bigger towns.
San Quirico is located between Pienza and Montalcino, so I think it’s perfect for a short break—or even better, to do what we did and book an accommodation near the town. This way, you’ll be closer to the heart of all the Val d’Orcia Tuscany beauty.
If your Val d’Orcia itinerary is packed, San Quirico is an ideal place to grab a coffee, enjoy a light meal, or stretch your legs while soaking in the local rhythm before heading to your next destination.
Another thing I loved about San Quirico was its relaxing evening atmosphere. I feel like this town embodies the spirit of a slow travel destination. While enjoying our dinners in cozy restaurants, we relaxed and people-watched all around us.
We saw groups of friends stopping to drink wine, eat pizza or pasta, and chat as they enjoyed their evening. Elderly locals were out dining and socializing, while a small number of tourists wandered the streets taking photos and exploring hidden corners.
I loved the tranquil atmosphere and serenity that surrounded us, and the simple way the locals seemed to enjoy life. There was no rush; everything moved at a slower pace—which was perfect for us, especially since we were right in the middle of our 10-day Tuscany road trip in Val d’Orcia.
So if you’re looking for a slow travel destination in Tuscany, or just a refreshing pause, San Quirico is without a doubt one of the best towns in Val d’Orcia.
Things to do in San Quirico d’Orcia
- Visit the Collegiata di San Quirico and admire its unique portals.
- Stroll through the Horti Leonini gardens – peaceful, beautifully designed, and perfect for a relaxing break.
- Explore Chiesa di Santa Maria Assunta – a simple yet atmospheric Romanesque church.
- Walk along the medieval walls for glimpses of the rolling countryside.
- Enjoy a slow meal or espresso in Piazza della Libertà – the perfect spot for people-watching and soaking in local life.
- Browse artisan shops for handmade Tuscan products like olive oil and ceramics. With fewer crowds here than in other towns, you’ll have more time and space to explore the shops and choose the perfect gifts.
Bonus tip: Just outside San Quirico, you’ll also find some of Val d’Orcia’s hidden gems—its most famous thermal springs: Bagno Vignoni, with its historic square centered on a steaming hot pool, and the more wild, natural Bagni San Filippo.
Monticchiello– A postcard town
Charming Streets and Medieval Atmosphere
This may sound unexpected, but Monticchiello was my favorite town, and this is why I’ve included it on my list of the best towns in Val d’Orcia.
You won’t find Monticchiello in many travel recommendations, because it’s a smaller village with fewer attractions compared to other Tuscan towns.
But in my eyes, this village felt like a miniature version of Tuscany’s medieval charm—with its quiet alleys and stone houses adorned with flower-filled balconies. While walking the narrow streets, you get a sense of intimacy that the bigger towns often lack.
When other towns impress with unique architectural details or imposing historical buildings, Monticchiello captivates with its simplicity and authenticity.
For me, Monticchiello is one of the true Val d’Orcia hidden gems.
Perfect postcard town – Tuscan hidden gem
Do you remember the era of postcards, when we used to see glimpses of dreamy places around the world that looked almost unreal?
Well, that’s exactly how Monticchiello felt for me—like a postcard brought to life. I fell in love from the moment we arrived, greeted by views of rolling hills and cypress-lined roads that looked like a painting, too perfect to be real.
We spent a few hours exploring the village on foot, and honestly, every corner and every turn felt like a photo opportunity. I admired the flowerpots on windowsills, the stone archways, and the charming little piazzas. For me, it was truly a fairytale town.
Being smaller and less popular than the other towns I mentioned, Monticchiello has fewer crowds, which means you can take your time, wander slowly, and capture the atmosphere at your own pace. If you love taking picturesque photos, this is the perfect chance.
In many ways, Monticchiello feels like Tuscany’s best-kept secret.
Things to do in Monticchiello
If you want a few specific goals while exploring Monticchiello, here are some ideas:
- Visit the Church of Santi Leonardo e Cristoforo, a small Romanesque church.
- Stroll through the medieval streets and take as many photos as you like.
- Eat traditional Tuscan food at Monticchiello’s highly regarded osterias, where authenticity is the key ingredient.
- Pause at the entrance of the village for breathtaking views of the Tuscan landscape and panoramic photo opportunities.
- Shop at local artisan stores for handmade items, olive oil, or other authentic Tuscan products.
Map & How to Visit These Towns
Overview map with marked towns
Val d’Orcia has so much to offer for all types of travelers. There are towns, viewpoints, monasteries, fortresses, and even thermal springs—so many that you’ll need a map to stay organized and make sure you don’t miss anything.
Because this article focuses on the best towns in Val d’Orcia, I’ve created a useful map that you can use with each village presented here.
If you’d like access to the full map with all the sights and experiences you can enjoy in Val d’Orcia Tuscany, consider subscribing to my newsletter. This way, you’ll get updated the moment I publish my complete Val d’Orcia travel guide.
Back to the best towns in Val d’Orcia: please use the map below to plan your itinerary. Having this visual will help you understand the order in which to visit, choose the best location to book accommodation in Val d’Orcia, and discover extra opportunities along the way.
Driving tips, distances, and parking challenges
Driving tips
I believe there are two main ways to visit the best towns in Val d’Orcia:
- by booking guided tours from bigger cities like Florence or Siena, or
- by renting a car and exploring on your own.
I highly recommend the second option. A Tuscany road trip in Val d’Orcia is such a beautiful and memorable experience that you’ll want the freedom to explore at your own pace, and to discover the hidden gems that guided tours often skip.
The roads through Val d’Orcia are incredibly scenic, and while driving you’ll be tempted to stop often for photos or simply to admire the rolling Tuscan landscapes.
👉 If you want to check prices or availability for car rentals, you can look [here].
Main driving tips for your Val d’Orcia itinerary:
- The roads are narrow, winding, and often without barriers. Drive slowly and cautiously—these roads aren’t made for speed.
- ZTL (Limited Traffic Zones): If you’ve ever driven in Italy, you know these zones can be tricky. They restrict access unless you’re staying inside the zone and have special permission. Many towns, including Pienza and Montepulciano, have ZTL in their historic centers.
- Take your time. Driving in Val d’Orcia isn’t just a way to get from point A to point B—it’s part of the experience. Don’t rush. Stop often, take photos (you’ll find countless opportunities), and make the road itself part of your journey.
Distances Between Towns
Val d’Orcia looks big on the map, but in reality, the towns are fairly close to one another:
- Pienza → San Quirico d’Orcia: ~10 minutes
- Pienza → Montepulciano: ~15 minutes
- Pienza → Montalcino: ~35 minutes
- Monticchiello → Pienza: ~10 minutes
👉 This means you can easily combine 2–3 towns in a single day without feeling rushed.
Parking challenges
Parking in Val d’Orcia can sometimes be as tricky as navigating ZTL zones. Most towns restrict traffic in their centers, so you’ll need to rely on free or paid parking outside the historic walls.
Here are a few things we learned:
- Small historic centers. Almost all towns have pedestrian-only areas, so expect to park outside the walls.
- Limited spaces. Parking fills up quickly, especially in Pienza, Montepulciano, and Montalcino during peak hours. Arrive early in the morning or later in the afternoon for the best chance.
- Paid parking. Most towns have pay-and-display lots near the entrances (€1–2 per hour). Bring coins, though many machines now accept cards.
Final Thoughts – My Favorite Town in Val d’Orcia
For me, every town in Val d’Orcia Tuscany is special and has a unique place in my heart. It’s hard to choose a favorite, because each one charmed me in a different way, and even if I try, it’s almost impossible to pick just one.
That being said, I think Monticchiello and Pienza stand out as the best towns in Val d’Orcia. Monticchiello felt like a true hidden gem—a postcard-perfect village that makes you fall in love with its medieval intimacy. Pienza, on the other hand, felt romantic, majestic, and impressive, with its perfect Renaissance details.
But of course, my preferences are very subjective. This is why I encourage you to see them all, and if you can, spend a few days here just breathing the Tuscan air, drinking the local wine, and capturing unforgettable photos.
✨ No matter which town you choose, Val d’Orcia will stay with you forever—like a timeless memory of Tuscany’s most beautiful soul.
Practical Note for Travelers
If you’re planning your trip and wondering when to visit Val d’Orcia, the best times are spring (April–May) for green hills and wildflowers, and autumn (September–October) for the harvest season and wine festivals.
As for where to stay in Val d’Orcia, you’ll find plenty of charming agriturismos, boutique hotels, and cozy guesthouses—perfect bases for exploring the region at a slow pace.
And if you’d like a complete resource with itineraries, travel tips, food & wine experiences, and more, don’t miss my upcoming Val d’Orcia Travel Guide.
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