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Winding road lined with cypress trees across golden rolling hills of Tuscany
Destinations

Val D’Orcia, Tuscany

In the heart of Tuscany, a stunning setting where unspoiled nature coexists harmoniously with regional history and traditions.

June 2025Florence & TuscanyBy Vanessa Bottero10 min read

The sweeping hills of Val d'Orcia are one of Tuscany's most famous landmarks. Since 2004, the Roman Via Francigena, its associated monuments (abbeys, inns, shrines, bridges), cities, villages, and farmhouses have all been recognized by UNESCO as part of an agricultural and pastoral landscape that showcases creative land management techniques. Val d'Orcia, in fact, encompasses a vast and beautiful area of Tuscany's southern countryside, near the border with Umbria and the Mount Amiata slopes. The Cypress is the iconic tree of this area, that’s why a visit to the Cypresses of San Quirico d'Orcia is a must-do.

Pienza, known as the "ideal city" of the Renaissance, is a true jewel set in the hills of Val d'Orcia. Stroll through the cobblestone streets, discover the old buildings, and take in the spectacular views from the panoramic terraces. Don't forget to try the famed Pecorino di Pienza. The Oak of Checche, located in the municipality of Pienza, is a monumental oak (Quercus petraea). The checca, or cecca, is the name used in Tuscany to indicate the magpie.

Bagno Vignoni, a unique settlement known for its thermal waters, which have been used since Roman times. Located along the Via Francigena, the village's center is dominated by a big thermal bath, creating an exquisite and timeless environment. This wonderful setting provides a peaceful and revitalizing experience.

The Chapel of the Madonna di Vitaleta, one of Val d'Orcia's most photographed scenes, it has been captured on innumerable postcards. This little chapel, situated between Pienza and San Quirico d'Orcia, captivates with its simplicity and the splendor of the surroundings.

The Abbey of Sant'Antimo, one of Tuscany's most evocative Romanesque churches, close to Montalcino. The abbey, which was supposedly established during Charlemagne's reign, is a serene and spiritual setting where Gregorian music can be heard. This stunning location exudes an unparalleled tranquility.

Val d'Orcia cypresses are famous, and they are frequently depicted in photography and paintings. One of the greatest spots to see them is in Quirico d'Orcia, specifically along the Via Cassia in the neighborhood "Triboli". The GPS coordinates are 43°03'45.6 N, 11°33'31.86 E. This location, which changes colors throughout the seasons, is ideal for taking the perfect photo.

A cypress-lined gravel drive leading to a Tuscan farmhouse

The Castle of Spedaletto, a fortified architectural complex located in the homonymous rural town of Pienza.

Castiglione D’Orcia, a delightful village that may surprise you. The main attractions include the Church of Santa Maria Maddalena, the Rocca Aldobrandesca, the Pieve of Saints Stefano and Degna, the Sala d'Arte San Giovanni, which is housed in the Confraternity of San Giovanni's seat, and Piazza Vecchietta with a stunning 16th-century travertine well.

A stone street with flowered balconies in a Val d'Orcia village

Montalcino , well-known around the world for its famed Brunello, one of the greatest red wines. However, this town has much more to offer, including a medieval fortress, scenic streets, historic churches, and museums with art collections.

Montepulciano, a lovely medieval town. Of Etruscan origin and recognized for the production of Vino Nobile (DOCG), is the perfect set for a delightful walk uphill to the Piazza Grande. Along the 16th-century road to the top, there are cafes and wine bars, aristocratic buildings like Palazzo Cervini and the Casa di Poliziano, and panoramic views of the valley.

Radicofani, one of five towns in Val d'Orcia designated as a UNESCO World Heritage Site, it also holds the Touring Club's orange flag. It is crossed for 15 kilometres by the historic Via Francigena, a commercial and religious artery that led from the north to Rome. The fortress and the village of Radicofani are located on a rocky volcanic rock at more than 800 meters above sea level, a strategic position because it dominates all the surrounding valleys.

San Quirico D’Orcia, an ancient walled settlement in the middle of the picturesque Val d'Orcia, halfway between Pienza and Montalcino. It is undeniably one of the most beautiful cities in the province of Siena, with various monuments to see and attractions strewn around. San Quirico's central location in the valley makes it an excellent starting point for exploring the surrounding area.

Monticchiello, halfway between Pienza and Montepulciano, is a little, charming, timeless ancient Tuscan village set on a hill, off the most popular tourist routes. Part of the historic walls remains intact, with 13th-century towers and casemates visible. A very beautiful 13th-century church with romanesque-gothic facade dedicated to saints Leonardo and Cristoforo. Walking through the hamlet lanes to the square, where the famed "Teatro Povero" of Monticchiello performs every summer, is a very memorable experience.

5 unmissable and iconic experiences in Val D’Orcia to discover the traditional culinary art:

  • Cheese workshops;
  • Pizza or bread making lessons;
  • Pasta cooking classes;
  • Tasting and wine tours;
  • Truffle hunts.

To personalize your trip, feel free to write us at info@zestitalytours.com

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