Among breathtaking landscapes, the Tuscan countryside, especially the Val d’Orcia, boasts some of the most beautiful views in the world. With its vast expanse and charming Tuscan villages, it’s easy to see why this region tops the travel wish list for international  and italian visitors.

Tuscany countryside is unmatched in Europe. Rolling wheat fields, lush forests, narrow roads lined with cypress trees, and rustic stone farmhouses create a classic regional scene. This enchanting landscape invites you to savor a glass of wine, a bite of cheese, and countless other local specialties born here.

So iconic is this scenery that UNESCO has designated it a World Heritage Site seven times, including the Val d’Orcia region itself.

Stretching between the Orcia River south of Siena and the border of Siena and Grosseto, the Val d’Orcia is best explored at a leisurely pace. But with so many Tuscan villages to visit, it’s easy to feel overwhelmed and miss some of the most picturesque views or unique attractions.

The Most Beautiful Tuscan Villages in Valle d’Orcia

This article was written in collaboration with Gabriele from Italia Ignota, a great friend who provided invaluable help in organizing my Val d’Orcia journey.
I highly recommend following his Instagram for daily discoveries of hidden Italian gems, especially lesser-known Tuscan landscapes untouched by mass tourism.

Pienza

Pienza is one of the most charming Tuscan villages, blending history, culture, art, and gastronomy. It’s the birthplace of Enea Silvio Piccolomini, later Pope Pius II, who transformed his hometown into a Renaissance dream with architect Bernardo Rossellino.

Construction began around 1459, and in 1996 UNESCO recognized Pienza’s historic center as a World Heritage Site. Notable Renaissance architecture includes the Assunta Cathedral, Palazzo Piccolomini, Palazzo Borgia, and Palazzo Gonzaga.

The vibrant flowers, quaint alleys, and hidden corners captivated me. Even with crowds, Pienza offered peaceful spots to discover. Don’t miss walking through “Casello,” the town’s smallest yet most charming quarter, featuring lanes like Via del Bacio, Via dell’Amore, and Vicolo Cieco.

We enjoyed lunch at Sperone Nudo, a delightful restaurant in Piazza di Spagna. Though stumbled upon by chance, it exceeded expectations! I highly recommend trying the pici pasta and local sausage, as well as the liver pâté—one of my favorites! Naturally, everything was paired with plenty of local red wine.

Pienza is also a cheese lover’s paradise. Be sure to sample the truffle Pecorino!

Chapel of Madonna Vitaleta in Valle d’Orcia

The road connecting San Quirico d’Orcia and Pienza is stunning—perfect for a bike ride, though we traveled by car. This route offers captivating landscapes with dirt roads, cypress trees, and charming farmhouses.

Despite the chapel being closed, the scenery made the stop worthwhile. The car park is about 300 meters away, and the short walk reveals a magical setting.

San Quirico d’Orcia

Situated on a hill between Pienza and Montalcino, San Quirico d’Orcia greets visitors with a row of cypress trees standing tall like sentinels—an iconic photography spot often bustling with tourists.

In medieval times, it was a crucial stop along the Via Francigena, the pilgrimage route connecting Northern Europe to Rome. Most of the town’s fortified walls remain, and cars are not allowed inside, so park outside the walls and explore on foot. One highlight is the Renaissance Horti Leonini gardens.

Montalcino

Park below the town and wander through its historic streets. Montalcino boasts an impressive museum, quaint shops, and panoramic views from its hilltop perch. However, food and wine lovers visit primarily for the renowned Brunello di Montalcino DOCG wine, one of Italy’s finest.

Abbey of Sant’Antimo

Just outside Montalcino, the Romanesque Abbey of Sant’Antimo sits in a picturesque setting and houses a public library. With careful planning, visitors can experience the monks’ chants—a rare and moving experience.

Chants take place daily at 9:00 am, 12:45 pm, and 2:45 pm, with a complete schedule posted at the Abbey entrance. Please refrain from taking photos or videos during the chants to respect the monks’ prayer.

Bagno Vignoni by Gabriele di Italia ignota

Bagno Vignoni is a must-visit for anyone exploring Val d’Orcia.

This tiny Tuscan village near the Via Francigena is famous for its thermal waters in Piazza delle Sorgenti. Historically, it was a luxury retreat for figures like Saint Catherine of Siena, Lorenzo de Medici, and Pope Pius II. The mineral-rich waters were renowned for their healing properties, first recognized by the Etruscans and later by the Romans.

Despite having only 30 residents, the village exudes charm. The sound of flowing water, Renaissance buildings, and Santa Caterina’s loggia create a fairytale atmosphere. The nearby Parco dei Mulini, where thermal waters cascade down a beautiful cliff overlooking the valley, is a sight to behold.

Castiglione d’Orcia by Gabriele di Italia ignota

Castiglione d’Orcia is one of the most beautiful Tuscan villages in Val d’Orcia, second only to Pienza and Montalcino. Perched on a ridge, it offers stunning landscapes and artistic treasures.

At the heart of the village stands the medieval Rocca degli Aldobrandeschi. The main square, Piazza il Vecchietta, is dedicated to painter Lorenzo di Pietro and features a central fountain and cobblestone pavement arranged in geometric patterns.

Nearby, the Rocca di Tentennano dominates the landscape, offering a commanding view of the Via Francigena and Orcia Gorge. Just a 1 km walk from the village, the panoramic view is well worth the trek.

If you have any questions or a favorite spot in Val d’Orcia that isn’t on our list, feel free to leave a comment below!

Go on traveling!

Lety goes on

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