The charm of timeless places, where beauty slips into your heart like a melody and lingers there to cradle memories: Val D'Orcia is like that. You may arrive for a weekend, but you leave in love forever. Geographically located in the southernmost part of Tuscany, this land, enclosed by gentle hills, stretches between the border with Umbria and the slopes of Mount Amiata, traversed by the Orcia River, from which it takes its name. Since 2004, its splendid landscape, characterized by views of great historical and artistic impact and lush nature, has been recognized as a UNESCO World Heritage Site for the way it combines medieval villages, panoramic roads, and natural sites of interest. If you're planning a few days to discover the wonders of Val D'Orcia, here are some must-visit stops.
Val D'Orcia and its villages: here's what to see
The history of Val D'Orcia begins with the birth of medieval villages that still form the basis of its settlement system. Founded between 1000 and 1100 along the Via Francigena, the typical towns of the valley developed around castles and fortified areas that have preserved the unchanged atmosphere that visitors from around the world fall in love with. These villages represent the pulsating heart of the cultural development that has characterized the region over the centuries. It's no coincidence that the Renaissance Ideal City, Pienza, arose in Val D'Orcia. Our journey to discover this historically rich land begins here.
Pienza
Founded by Pope Pio II, who was born into a noble family in Siena, Pienza is a small wonder framed by the Tuscan hills. Pio II rethought its urban structure according to Renaissance architectural principles, assigning the realization to Matteo Gambardelli, known as Il Rossellino, a student of Leon Battista Alberti. The village became the Renaissance Ideal City, intertwining urbanistic dimensions and humanistic conception. For these reasons, UNESCO recognized its universal value in 1996, inscribing it among the World Heritage Sites.
Visitors are captivated by the splendor of Palazzo Piccolomini, which, in addition to its precious interiors, boasts a rooftop garden with a splendid view of Val D'Orcia. A visit to the village of Pienza must include a stop at Palazzo Comunale, appreciated for its iconic loggia that characterizes the facade. Among the gems of this beautiful town in Val D'Orcia is Palazzo Massaini, built on a hillside, standing on the ruins of a medieval castle. Exploring the surroundings of Pienza also offers the opportunity to admire the Pieve di Corsignano, an ancient place of worship that was a crucial stop for pilgrims on the Via Francigena.
Castiglion d'Orcia
Among the most beautiful villages in the valley is Castiglion D'Orcia. The heart of this town, located at an altitude of 540 meters, revolves around the square dedicated to the painter Lorenzo di Pietro, known as Il Vecchietta. Dominated by the powerful Aldobrandeschi family and later becoming a free commune, in the 14th century, the village came under the jurisdiction of the Republic of Siena, which entrusted control to the Piccolomini and later to the Salimbeni. Places of interest to include in your itinerary are the Pieve dei Santi Stefano and Degna and the ruins of the Rocca Aldobrandesca. The ancient fortress, which dominates the hill on which the village stands, still allows glimpses of extensive portions of walls and the keep, largely preserved.
The Cypress Trees of San Quirico and Borgo Vignoni: two icons of Val d'Orcia
Val d'Orcia also has a popular face made iconic by countless photographs that have circulated around the world. Those who have been in the valley at least once know: you can't leave without capturing the profile of the hills framed by the famous cypress trees of San Quirico. A symbol of the entire Tuscan region, this landscape welcomes tourists who are about to visit the small medieval village known for the beautiful collegiate church of San Quirico and Giuditta and the splendid Horti leonini, gardens created by Diomede Leoni in 1540. Among the most appreciated and photographed places is Bagno Vignoni: the ancient thermal village is characterized by the spectacular Piazza delle fonti, a kind of pool where the 16th-century buildings are reflected.
Montepulciano
A tour of Val D'Orcia is incomplete without a visit to Montepulciano, the land of Vino Nobile. To breathe in the ancient atmosphere of this town with a viticultural vocation, just reach Piazza Grande: here, at the highest point of the village, the suggestive square frames the main historical palaces, medieval buildings renovated between the 15th and 16th centuries following the principles of Florentine and Roman Renaissance architecture. Among them stands out the 14th-century Municipal Palace, which offers a breathtaking view of Mount Amiata, Lake Trasimeno, and Mount Subasio. Commissioned by Cosimo I De' Medici, the building is famous for the crenellated tower reminiscent of the Palazzo della Signoria in Florence.
Taste the Vino Nobile: stop at Fattoria del Cerro
Naturally, you can't leave Montepulciano without savoring its most famous product: Vino Nobile. So why not plan a visit to a winery, perhaps allowing yourself a couple of days of relaxation in the Tuscan countryside? For those who want an immersive experience in wine, good food in a welcoming and refined setting, Fattoria del Cerro is the right choice. Located in Acquaviva, the estate offers a unique opportunity to observe up close the production stages of Vino Nobile di Montepulciano DOCG, produced here with the label "Silìneo" and in reserve version. Visitors can follow a tasting route in the barrel room and then discover the flavors of Tuscan cuisine through dishes prepared by the chef of Villa Grazianella. The elegant Relais has eleven rooms overlooking the estate, perfect for a restful night before setting out to explore the beautiful valley. To explore the spaces of Villa Grazianella and perhaps choose your room, you can also take a virtual tour: just follow the link available in the "hospitality" section of the Fattoria del Cerro website.
Val D'Orcia is a land rich in charm: among ancient villages, nature, and flavors, it's the perfect destination for a mini vacation away from city rhythms. Have you already planned your itinerary?
