Discovering the Val d’Orcia: 6 dream itineraries in the villages and hills

The first itinerary is a real “picture postcard” start. You set off from Pienza, known as the ideal Renaissance town. Walking through its streets is already a little journey back in time, but the magic really begins when, after reaching the ancient Romanesque Parish Church of Corsignano, you take the road known as Strada del Gladiatore (Gladiator Road). This dirt road, alongside which you will see rolling hills and solitary cypress trees, seems deliberately made for walking slowly and stopping to admire every view.

Along the way, you will come across Podere Terrapille, an ancient farmhouse surrounded by fields and lastly Bagno Vignoni, with its thermal pool-square that seems like something straight out of a painting. Here, you can treat yourself to a relaxing break in the hot waters.

• Length: 11–12 km
• Duration: 3-3.5 hours
• Advice: Always have your trekking shoes, water and camera ready.

This itinerary is short but intense. From San Quirico d’Orcia, a medieval village nestled between the hills, you walk uphill towards the Chapel of Vitaleta, a little gem suspended between the land and the sky. From here, there is a spectacular view of the rolling hills and cultivated fields of the Val d’Orcia. The path continues to Pienza, treating you to endless views to photograph.

• Length: 10 km
• Duration: about 3 hours
• Advice: This is an excellent route for photographers and lovers of iconic views; bring a hat and sunscreen.

A route that combines history, villages and thermal baths. From San Quirico, you walk uphill to Vignoni Alto, an ancient medieval village that seems suspended in time, with narrow lanes and incredible views. The descent leads to Bagno Vignoni, where the hot thermal waters are a real reward after the walk.

• Length: 11 km
• Duration: 3-3.5 hours
• Advice: This path is suitable for everyone, perfect for a morning walk with a stop for relaxing at the end.

This itinerary is for those who love exploring the most authentic villages. Setting off from Bagno Vignoni, you walk uphill towards Rocca d’Orcia, a small hilltop village with spectacular views. The walk continues to Castiglione d’Orcia, a medieval village dominating the valley, where history and nature blend together harmoniously.

• Length: 12 km
• Duration: 3.5-4 hours
• Advice: Bring snacks, water and suitable shoes for gentle uphill climbs and a camera is essential.

A short but equally captivating itinerary. From Pienza, through the rolling hills and along dirt roads, you come to Monticchiello, a medieval village surrounded by walls and the warm colours of the Tuscan countryside. Every lane and every view is perfect for stopping and breathing in the authenticity of Tuscany.

• Length: 8 km
• Duration: 2-2.5 hours
• Advice: It is excellent for leisurely walks; a lunch break in the village is recommended.

From Montalcino, the home of Brunello wine, the itinerary leads to the Abbey of Sant’Antimo, one of the most enchanting Romanesque gems in Tuscany. The path, which is almost flat, crosses vineyards and rows of cypress trees, treating you to a unique view of the valley. Once you get to the abbey, every step you have walked is rewarded by the silence and majesty of the building.

• Length: 6–7 km
• Duration: 1.5-2 hours
• Advice: This is ideal for a relaxing walk; take water and comfortable shoes with you.