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Val d'Orcia walking • From Montepulciano to Siena
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Duration :
8 days
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Apr May Jun Jul Aug Sep Oct
price in double room from: € 926
Val d'Orcia walking • From Montepulciano to Siena

Val d'Orcia walking • From Montepulciano to Siena

Hilltop towns of Tuscany

  • Natural, artistic and cultural treasures of Val d’Orcia, a UNESCO World Heritage Site
  • Wide-open fields, cypress-lined hills, famous vineyards
  • Exquisitely preserved Medieval and Renaissance villages
  • Peaceful country roads, friendly Tuscan locals and delicious regional specialties
Map walking routes Val D'orcia
View map

The route is quite easy, with ups and downs typical of the Tuscany’s rolling hills. The whole itinerary is mostly on paths and gravel roads (strade bianche), even if you will find some sections on asphalted road.  Some walks can be shortened if requested in advance.  

Start: Montepulciano                Finish: Siena

Day 1: Arrival in Montepulciano
Day 2: Walk from Montepulciano to Pienza (13 - 15 km / 8 - 9,5 mi)
Day 3: Walk from Pienza to Bagno Vignoni (12 km / 7,5 mi)
Day 4: Transfer to Castelnuovo dell'Abate, walk to Montalcino (13 km / 8 mi)
Day 5: Walk from Montalcino to Buonconvento (15 -18 km / 9,5 - 11 mi)
Day 6: Loop walk to Monte Oliveto Maggiore Monastery (14 km / 8,5 mi)
Day 7: Transfer to Monteroni d’Arbia, walk to Arbia & train to Siena (10 km/ 6 mi)
Day 8: Departure from Siena

Day 1:    Arrival in Montepulciano

Your Tuscan walking begin in the medieval and Renaissance hill town of Montepulciano. Montepulciano is easily accessible via Rome, Florence or Pisa; catch the train to Chiusi then take a local bus or a short taxi ride to Montepulciano. Admire the impressive views over the rolling Tuscan landscape that you’ll be exploring over the next week. 

Day 2:    Walk from Montepulciano to Pienza (13 - 15 km / 8 - 9,5 mi)

Set off from San Biagio church on a quiet rural track and suddenly you’re lost in peaceful beauty. Soon you come upon the peaceful village of Montichiello, where you can pause for a relaxed lunch or perhaps just a quick cappuccino on the way to Pienza.
Picture-perfect Pienza is a UNESCO World Heritage Site brimming with unique Renaissance architecture. AND it is home to delicious pecorino cheese and tasty truffles. The ideal spot to indulge in Tuscan treats!

Challenge: 4 hours, 13 - 15 km / 8 - 9,5 mi, 385 m ascent, 505 m descent

Day 3:    Walk from Pienza to Bagno Vignoni (12 km / 7,5 mi)

Wander through impossibly perfect landscapes of rolling hills, majestic oaks, cypress trees and photogenic villages. Stop to rejuvenate at the hot springs in Bagno Vignoni and trade the warm Tuscan sun for steaming medicinal waters.

Challenge: 4 hours, 12 kmv / 7,5 mi, 195 m ascent, 420 m descent

Day 4:    Transfer to Castelnuovo dell'Abate, walk to Montalcino (13 km / 8 mi)

Today you will walk mainly on wide dirt roads. As you arrive in the village Castelnuovo dell’Abate take your time to enjoy the stunning beauty Sant’Antimo Abbey, a former Benedectine monastery dating back to the 8th century A.C. The first part of the route to Montalcino is extremely panoramic, with fabulous
views over the Orcia valley while the last few km are in the woods. As you arrive in Montalcino, relax and enjoy one of the exquisite local wines.

Challenge: 13 km / 8 mi , 450 m ascent / 280 m descent

Day 5:    Walk from Montalcino to Buonconvento (15 -18 km / 9,5 - 11 mi)

A hearty breakfast will set you up for a long but enjoy day of  walking in the famous Brunello wine region, passing vineyards and olive groves, then again entering the beautiful Tuscan landscape of the Crete Sensi and Buonconvento.

Challenge: 5 hours, 15 -18 km / 9,5 - 11 mi, 316 m ascent, 619 m descent

Day 6:    Loop walk to Monte Oliveto Maggiore Monastery (14 km / 8,5 mi)

A short day which is full of ups and downs, beginning with a transfer to the monastery at Monte Oliveto Maggiore, an impressive abbey built of red brick and set in the rugged Tuscan landscape. After an early visit to avoid the crowd, walk back to Buonconvento.

Challenge: 5 hours, 14 km / 8 mi, 382 m ascent, 460m descent

Day 7:    Transfer to Monteroni d’Arbia, walk to Arbia & train to Siena (10 km/ 6 mi)

A short transfer takes you to Monteroni d’Arbia then you head toward Siena on foot, hiking hills and hamlets till the city's unmistakable silhouette begins to materialize in the distance. At Arbia you catch the train into Siena, then spend the evening wrapped in its magnificent beauty: the grand Piazza del Campo, delightful Duomo and medieval palaces recalling the city’s ‘contrade’ who ride in the risky ‘il Palio di Siena’.

Challenge: 4 hours, 10 km / 6 mi, 225 m ascent, 185 m descent

Day 8:    Departure from Siena

Your self-guided walking holiday comes to an end today after breakfast. Departure from Siena.


We use selected 3* and 4* hotels and agriturismo.  Some of the accommodations chosen have a swimming pool and internal restaurant.  They have been carefully selected for their location, atmosphere and/or unique services. All rooms are en-suite. Some of the hotels we work with appear here. If a certain hotel is unable to confirm due to lack of availability, we will request a similar one and inform you about the alternative booked. 

Extra nights: Extra nights can be booked at any of the accommodations along the way.

Hotel Il Duomo (Montepulciano)
Hotel Il Duomo (Montepulciano)

The Duomo hotel, in Montepulciano’s old town centre near the Piazza Grande, is a small, welcoming family-run hotel situated in an old Renaissance Palazzo. What sets the Duomo apart is the attention we pay to our guests, creating a relaxing and intimate atmosphere for the duration of your stay.


Piccolo Hotel La Valle (Pienza)
Piccolo Hotel La Valle (Pienza)

Walking along the city walls of the town of Pienza in the direction of the Val d’Orcia, there is a building made of stone and brick, Il Piccolo Hotel La Valle. Its strategic position, a stone's throw from the historic center and its panoramic garden patio makes it an ideal place to have a magic and relaxing stay immersed among culture, unspoiled nature, gastronomy & handcrafters. There are numerous activities and experiences that can be enjoyed while spending a vacation in one of the most fascinating areas of Tuscany.


B&B La Locanda del Loggiato (Bagno Vignoni)
B&B La Locanda del Loggiato (Bagno Vignoni)

This isn’t an ordinary bed & breakfast in Val d’Orcia, it isn’t just a ‘place to sleep’, it’s a refuge where charm and romanticism blend with simplicity. The Locanda del Loggiato dates back to 1300, it will take you back in time and allow you to discover the delights of one of the most magical spa villages in Tuscany, Bagno Vignoni.


Albergo Il Giglio (Montalcino)
Albergo Il Giglio (Montalcino)

Il Giglio open at the end of 19th century, as a coach house, where travelers could find a place to eat and sleep, and horses could rest after the steep climb to Montalcino.


Agriturismo Pieve a Salti (Buonconvento)
Agriturismo Pieve a Salti (Buonconvento)

The Borgo of Pieve a Salti is nestled in the rolling hills of Siena, in a beautiful natural setting, rich in history, art and sacred traditions. Its houses, inside the old village overlooking the surrounding hills, offer you hospitality in comfortable rooms with bathroom or typical apartments of various sizes .


Hotel Chiusarelli (Siena)
Hotel Chiusarelli (Siena)

Hotel Chiusarelli is located right in the historical centre of Siena, city of art that still nowadays remains rooted in its traditions, among which is the famous Palio. The hotel is set in a neoclassical villa built in 1870. The renovation has added a modern touch keeping, however, the original style of the palace that, with its magnificent frescoed rooms, makes our guests feel like stepping back in time.



Departure an day of the week, subject to availability, from April 1st until october 31st

The best arrival airports are Rome (FCO), Florence (FLR) and Pisa (PSA)

Arrival at Montepulciano


From the airports you can take a train and then busses to reach Montepulciano.  


From Rome

From the two major Rome airports take the bus or train to Rome Termini train station. From Roma  Termini train station take the direct train to Chiusi-Chianciano Terme (train ride takes approx. 1 hour and 40 minutes, ticket costs 9,95 Euros) From Chiusi-Chianciano Terme take the bus to Montepulciano (line FT4 bus ride takes 25 minutes) www.sienamobilita.it

From Florence

From Florence airport take the bus Florence Santa Maria Novella train station. From Florence train  station take the direct train to Chiusi-Chianciano Terme (train ride takes approx. 2 hours and 15 minutes, ticket costs 13,50 Euros) From Chiusi-Chianciano Terme take the bus to Montepulciano (line FT4 bus ride takes 25 minutes) www.sienamobilita.it

Departure from Siena


Check the updated timetables on the website www.trenitalia.com

To Pisa Airport: From Siena take the train to Pisa Centrale. Train journey to Pisa takes approx. 1 hour and 45 minutes, ticket costs 10,70 Euros. From Pisa Centrale you can take a bus, train or taxi to reach Pisa Airport. 

To Florence Airport: From Siena take the train to Florence Santa Maria Novella Train journey to Florence takes approx. 1 hour and 30 minutes, ticket costs 9,10 Euros. From Florence Santa Maria Novella you can take a bus or taxi to reach Florence Airport

If you are traveling with your own vehicle, you will be assigned another hotel that has parking, this would involve a small additional supplement.

GPS tracks are available on request




  • 7 Nights' accommodation in selected B&Bs, hotels and agriturismo with breakfasts
  • Luggage transfer (from day 2 to day 7)
  • Transfer from Castelnuovo dell'Abate to Montalcino (Day 4)
  • Transfer from Buonconvento-Monte Oliveto Maggiore Abbey (day 6) and from Buonconvento to Monteroni d'Arbia (Day 7)
  • Digital detailed route notes and maps in English
  • Access to the trip on our navigation app
  • 24-hour telephone assistance

Not included

  • Travel insurance
  • Travel to the firts accommodation in Montepulciano and from the last accommodation in Siena
  • Trains, busses or boats wherever necessary
  • Lunches & Dinners
  • Drinks and snacks
  • Personal equipment
  • Tourist taxes 

Optional services

  • Additional nights before, during or after the walk
  • Single Room Supplement(s)
  • Transfer from Arbia train station and transfer to Siena
  • Shipment of trip docs to your home address

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