
Villages & fortresses
Castiglione, Rocca d'Orcia and Radicofani
Visit the central valley and Rocca di Tentennano, then continue south to Radicofani and its historic Via Francigena stronghold. Check seasonal opening times before setting out.

A verified, practical itinerary · From Pienza
The cinematic heart first, then the villages, abbeys and southern valley
Val d'Orcia is not a single attraction but a cultural landscape of hill towns, working fields, rural roads, abbeys and historic thermal settlements. Since 2004, the territories of Castiglione d'Orcia, Montalcino, Pienza, Radicofani and San Quirico d'Orcia have formed the UNESCO World Heritage site. These itineraries begin in Pienza and grow naturally from one to three days.
Choose your time
Day 1
With only one day, stay between Pienza and Bagno Vignoni. This is where the two Gladiator locations, Vitaleta and some of the valley’s most recognisable scenery are concentrated.
Morning
Walk through Piazza Pio II, the Cathedral, Palazzo Piccolomini and the panoramic lanes of the Renaissance town. Pienza’s historic centre has been a UNESCO site since 1996.
Late morning
Walk from Pienza along Strada delle Fonti, pass the Pieve of Santi Vito e Modesto and continue through the working landscape towards Terrapille.
Afternoon
Check Vitaleta’s official closure calendar before visiting. Continue towards San Quirico and photograph Maximus’s private villa only from outside the gate.
Evening
See the Collegiata and Horti Leonini, then finish beside the thermal Piazza delle Sorgenti. Bathing in the monumental pool is prohibited.
The route visitors actually need
Any public car park in Pienza is suitable: the town is compact. From the centre, follow this locally verified route.
This is an active agricultural landscape. Stay on the path and uncultivated ground without trampling wheat or other crops. Leave no litter and do not cross closed gates or fences.
The villa is a separate location near San Quirico: 3J86+5R. Use the small pull-off opposite or the space outside the gate. Never enter the private field or pass through the gate.
Day 2
Keep day one around Pienza, then use the second day for the western side of the valley. Start at Bagno Vignoni if you did not visit it the evening before.
Walk around Piazza delle Sorgenti and see the historic Parco dei Mulini below the village.
02Explore Piazza del Popolo and the 14th-century fortress. Allow extra time only if you have booked a winery visit.
03Continue to Castelnuovo dell’Abate. Opening times vary by season and liturgical activity, so check the abbey’s official website that day.
Day 3
On the third day, choose one coherent direction instead of crossing the entire valley.

Villages & fortresses
Visit the central valley and Rocca di Tentennano, then continue south to Radicofani and its historic Via Francigena stronghold. Check seasonal opening times before setting out.

Water & Monte Amiata
Head towards Bagni San Filippo, in Castiglione d'Orcia, where hot springs feed the Fosso Bianco in the woodland. Check current municipal notices and follow all on-site restrictions.
One day covers Pienza, the Gladiator Field, San Quirico and Bagno Vignoni. Two days add Montalcino and Sant’Antimo. A third allows time for Castiglione, Radicofani or Bagni San Filippo.
Yes. Walk from Pienza towards Terrapille. The locally verified route is about 900 metres each way and passes the Pieve di Corsignano. Stay on the path and uncultivated ground without trampling crops.
No. The field is at Terrapille below Pienza. Maximus’s villa is a separate private property near San Quirico d’Orcia.
No. Photograph it only from outside the gate, using the available roadside spaces without entering the private land.
No. Bathing in the monumental pool in Piazza delle Sorgenti is prohibited; use authorised thermal facilities.
Historic and access information was checked against official tourism bodies, municipalities and the sites that manage each place. Recheck live opening information before travelling.