Val d'Orcia Trekking 4 Days: Villages, Cypresses and the Via Francigena

There are places best understood on foot. In Val d'Orcia, the landscape shifts with every bend: a white gravel road crosses the fields, a row of cypresses draws the eye toward a farmhouse, a village appears atop a hill. This four-day journey invites you to explore the valley at a relaxed pace, following trails that weave together nature, history, and rural life.

The base is Palazzo Conti, in San Quirico d'Orcia, where you'll stay for the entire program. From here, you'll reach different points of the valley each day, alternating scenic walks, small villages, and places tied to the history of the area. The program includes about 55 kilometers of walking in total, spread across four hikes.

The first day begins in Pienza and leads to the Cappella di Vitaleta, one of the most iconic sites in Val d'Orcia. 

The following day starts in San Quirico d'Orcia along a stretch of the Via Francigena. The route crosses the Sienese countryside and reaches Bagno Vignoni, a spa village clustered around its large water basin. Along the loop, you'll come across the old mills powered by thermal waters and Vignoni Vecchia, before returning to San Quirico once again following the Francigena.

The third hike connects Pienza to Monticchiello along the “Latte di Luna” loop, a name that recalls the pale tones of the clay biancane hills. Monticchiello retains the character of a small medieval village and offers a pleasant stop among its central streets.

On the last day, you'll walk in the Foce area, reachable by car from Pienza. The route crosses the Pietraporciana Nature Reserve, through woods and views over Val d'Orcia, and reaches Castiglioncello sul Trinoro. After visiting the village, the route closes by returning to the starting point.

Four different days, united by the pleasure of observing the landscape up close: following roads between the hills, stopping in villages, and discovering, at every stage, a new way of looking at Val d'Orcia.

Why join us:

• 4 different days, one common thread
• Authentic villages, not postcard clichés
• Evenings and dinners together, a group atmosphere
• A slow pace, made just to let you enjoy every bend

Get your boots ready: the Guidders are waiting for you in Val d'Orcia.