A self-guided walk through Tuscany’s hilltop wine towns, from Montepulciano to Siena, across the UNESCO-listed landscape of the Val d’Orcia.
5 Days / 4 Nights, or 8 Days / 7 Nights
Easy to Moderate
Val d'Orcia, Tuscany, Italy
Any day of the week, April to October
Around 50 km over 5 days, or around 90 km over 8 days
€620
The Val d’Orcia stretches around 80km through the heart of Tuscany, from Siena in the north to the slopes of Monte Amiata in the south. Rolling hills, cypress-lined roads and terraced vineyards run between hilltop towns that have changed very little since the Renaissance, and the whole valley was added to the UNESCO World Heritage list in 2004.
This route links three of the region’s best-known towns on foot. Montepulciano and Montalcino are both well known for their wine, Vino Nobile in one, Brunello in the other, while Pienza is a UNESCO town in its own right, rebuilt in the 15th century as an ideal Renaissance city. Along the way, the route also passes through Bagno Vignoni, where warm spring water has fed the town’s baths since Roman times.
Two lengths are available. The 5-day version runs Montepulciano to Montalcino. The 8-day version continues on from Montalcino, through the Crete Senesi landscape and past the Monte Oliveto Maggiore monastery, before finishing in Siena. Both end each day in a Tuscan town with a proper dinner in mind, not a packed sandwich on the trail.
Accommodation:
Three-star hotels and agriturismi, on a bed and breakfast basis, all rooms en-suite. Additional nights can be added at any of the accommodations along the route.
Meals:
Breakfast included every morning. Lunch and dinner aren’t included unless specifically listed for a particular day, but each overnight town has plenty of choice for both.
Availability:
Starts any day of the week, between April and October.
Difficulty:
Graded easy to moderate. Walking days run around 4 to 5 hours, mostly on quiet paths and dirt tracks through rolling countryside, with some steeper sections on the approach to hilltop towns. Suitable for most reasonably active walkers.
Settle into Montepulciano, a hilltop wine town of steep medieval streets and Renaissance palazzi. The easiest way in is by train to Chiusi, then a short local bus or taxi ride. Worth an evening in one of the town's wine bars, glass of Vino Nobile in hand, looking out over the hills you'll be walking through over the next few days.
Overnight: Montepulciano
Distance: 13 to 15 km, Ascent: 384 m, Descent: 504 m, Walking time: around 4 hrs
From the church of San Biagio, a quiet path runs through rolling countryside past wineries, vineyards and olive groves, with a stop possible in the small village of Montichiello along the way. Pienza itself has been a destination since the 1400s, rebuilt as a model Renaissance town around its pope's palace and cathedral, with sweeping views over the Val d'Orcia from the old town walls. Known locally for truffles and pecorino cheese.
Overnight: Pienza
Distance: 12 km, Ascent: 197 m, Descent: 418 m, Walking time: around 4 hrs
Soft hills, oak forest and cypress trees lead to Bagno Vignoni, where the town's warm thermal baths draw directly on underground springs that have been in use since Roman times. Good reason to spend the afternoon soaking tired legs before the next day's walk.
Overnight: Bagno Vignoni
Distance: 13 km, Ascent: 450 m, Descent: 280 m, Walking time: around 5 hrs
A short transfer brings you to Castelnuovo dell'Abate, home to the Sant'Antimo Abbey, a Benedictine monastery dating back to the 8th century. From there, wide dirt paths lead across panoramic hillside with views over the Orcia valley, before the final stretch through quieter woodland into Montalcino. The town, at 750m, is the home of Brunello di Montalcino, with wine cellars, cafes and craft workshops in the historic centre.
Overnight: Montalcino
Distance: 15 to 18 km, Ascent: 316 m, Descent: 619 m, Walking time: around 5 hrs
A longer day through the Brunello wine region, past vineyards and olive groves, into the distinctive bare clay hills of the Crete Senesi before reaching Buonconvento.
Overnight: Buonconvento
Distance: 14 km, Ascent: 382 m, Descent: 460 m, Walking time: around 5 hrs
A short transfer up to Monte Oliveto Maggiore, a Benedictine monastery founded in the 14th century and still an active religious community today, with most of the current complex dating from the 15th and 16th centuries. The walk back to Buonconvento passes through the village of Chiusure and more of the Crete Senesi landscape.
Overnight: Buonconvento
Distance: 10 km, Ascent: 227 m, Descent: 187 m, Walking time: around 4 hrs
A short transfer to Monteroni d'Arbia starts the last day of walking, crossing hilly terrain and a handful of small villages before a short train connection covers the final stretch into Siena, leaving plenty of time to explore the city itself.
Overnight: Siena
The walk ends here. Siena has good onward train connections to Rome, Pisa and Florence.
From
€620
per person
Sharing basis · High season supplement applies · Minimum 2 people per booking
