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Val d'Orcia, Montepulciano to Siena
Level :
Duration :
8 days
Aug Sep Oct
price from € 813
Val d'Orcia, Montepulciano to Siena

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Val d'Orcia, Montepulciano to Siena

Val d'Orcia, Montepulciano to Siena - 8 days

Val d'Orcia, Montepulciano to Siena - 8 days

The Tuscan landscape of the Val d’Orcia will warm your heart like a classic photograph as you penetrate its natural beauty. You are in for a thrilling ride along steep valleys, dense forests, rivers and the legendary “badlands” eroded clay slopes. Walk by picturesque farmhouses nestled amidst olive groves, vineyards and fig trees on your way to the hot spring hamlet of Bagno Vignoni and the heavenly Renaissance city of Pienza. You shall visit captivating palaces, Romanesque churches, thermal baths, and prestigious wineries serving the divine local red “Brunello”. Soaring up high on invigorating hilltop towns, you’ll revel in delight. 

Day 1: Arrive in Montepulciano
Day 2: Walk from Montepulciano to Pienza, 13 km
Day 3: Pienza to Bagno Vignoni, 12 km
Day 4: Transfer to Castelnuovo dell'Abate, walk to Montalcino, 13 km
Day 5: Walk from Montalcino to Buonconvento, 15 km
Day 6: Loop walk to Monte Oliveto Maggiore Monastery, 14 km
Day 7: Transfer to Monteroni d'Arbia and walk to Arbia, train to Siena, 11 km
Day 8: Depart from Siena

Day 1:     Arrive 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 km

Starting from the San Biagio church you follow a quiet track to the peaceful village of Montichiello where you can pause for a relaxed lunch or perhaps just a quick cappuccino before continuing to Pienza. Pienza is a UNESCO World Heritage site with unique Renaissance architecture. The town is well known for its delicious pecorino cheese and truffles; this is a grat spot to indulge in Tuscan treats! 

Distance: 13 km

Elevation: +384 / -504 m

Day 3:    Pienza to Bagno Vignoni, 12 km

Today you wander through a beautiful region of rolling hills, oak woods, cypress trees and pretty villages. The thermal baths complex at Bagno Vignoni is the perfect location to spend the afternoon soaking up the Tuscan warmth. 

Distance: 12 km

Elevation: +197 / -418 m

Day 4:     Transfer to Castelnuovo dell'Abate, walk to Montalcino, 13 km

A transfer will take you to Castelnuovo dell'Abate in the morning. A more challenging but rewarding day’s walking awaits as you follow dry riverbeds through a fairly wild environment to Sant’Antimo, an isolated abbey situated in a pastoral landscape.

Distance: 13 km

Elevation: +450/ -280 m

Day 5:    Walk from Montalcino to Buonconvento, 15 km

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 Senesi and Buonconvento

Distance: 15 km

Elevation: +316 / -619 m

Day 6:    Loop walk to Monte Oliveto Maggiore Monastery, 14 km

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

Distance: 14 km

Elevation: +382 / -460 m

Day 7:     Transfer to Monteroni d'Arbia and walk to Arbia, train to Siena, 11 km

Today you will start with a short transfer to Monteroni d'Arbia from where you start the walk to Arbia. Hike through a landscape of rolling hills and small hamlets as the unmistakable sight of Siena appears in the distance. It's an easy and scenic walk on dirt roads through the Crete Senesi. Along the route you can stop and visit the San Fabiano castle. A train will then take you from Arbia to Siena.

Distance: 11 km

Elevation: +227 / -187 m

Day 8:    Depart from Siena

Last day included. Tour ends after breakfast. 


Nights in double rooms in 3/4* hotels and agritourismi with breakfast

Hotel Il Duomo Montepulciano
Hotel Il Duomo - Montepulciano

Hotel Il Duomo is housed in a 16th-century building in Montepulciano's historical centre. It has not so spacious rooms, but clean and well-finished with satellite TV, minibar, private bathroom, free Wifi and heating. Breakfast is both sweet and savoury and during spring and summer it's served outside. Staff is welcoming and courteous.

Piccolo Hotel La Valle Pienza
Piccolo Hotel La Valle - Pienza

The Piccolo Hotel La Valle is equipped with all comforts and facilities, 15 well-kept rooms furnished in Tuscan classic style, some with balconies facing the Val d’Orcia, the garage for cars, motorcycles and bicycles. Customers will be welcomed and well looked after and thanks to its family management, care and selection of products, they will be able to discover the excellence of the area and at the same time feel at home.

B&B La Locanda del Loggiato Bagno Vignoni
B&B La Locanda del Loggiato - Bagno Vignoni

B&B Locanda del Loggiato is housed in a 14th century building in Bagno Vignoni, one of the most magical spa villages in Tuscany. Rooms are elegant, well-finished and comfortable, each one with own furnitures. These have free Wifi, own heating/air conditioning, terracotta flooring and old wooden beams. Staff is courteous and welcoming.

Hotel Giglio Montalcino
Hotel Giglio - Montalcino

It was obtained from an ancient palace built near the castle walls of the city of Brunello. At this point you look out over the Crete and Siena with a dizzying view. Il Giglio is a small three-star family run, with passion and simplicity.

Agriturismo Pieve a Salti Buonconvento
Agriturismo Pieve a Salti - Buonconvento

This Farmhouse is nestled in the rolling hills of Siena housed in an old tuscany building of the 19th century outside Buonconvento. Rooms are well-furnished with rustic style, not so spacious, but clean and comfortable with TV, minibar, air-conditioning. The restaurant is open at dinner and it offers biological tuscany cuisine. Staff is helpful.

Hotel Chiusarelli Siena
Hotel Chiusarelli - Siena

The three-star Hotel Chiusarelli is located in the city centre of Siena, finds its natural setting in a neoclassical villa built around 1870. The structure  has been completely renovated in 2013. Rooms are spacious and clean and these offer  bathroom with shower or bathtub, hairdryer, air conditioning/heater, telephone, Wi-Fi, TV with Sky Vision. The Hotel has no lift. High quality breakfast.

practical info

The  climate  in Tuscany  is  generally  very mild  with  differences  depending  on  the geography  of the  region,  from  coasts  and valleys to the continental areas.The warmest months are generally July and August,  with  temperatures  ranging  from 23°C up to 30°C; the valleys can often see higher  temperatures  and  38°C  to  40°  C  is not uncommon. While  June  and  September  offer  both  nice warm weather. Of course, there are always exceptions  or  dry  spells  that  cause  a  few days to get really hot.Spring    (April    and    May)    and    Autumn (October   and   November)   are   dry, with sunny  days  but  the  chances  of  rain  are high. The  weather  can  change  very  quickly  and you must be prepared forrain, mist, wind, fog   (and   even   hail   or   snow   at   higher elevations) –especially   in   spring and autumn. 

From Florence airport (FLR), take the bus to Santa Maria Novella train station and then a train to Chiusi Chianciano (and then take the bus to Montepulciano.

From Pisa airport (PSA), take the train to Chiusi Chianciano (with 2/3 changes, depending on time. 

On departure from Siena reach the train station.

Check train timetables on

GPS tracks are available on request.


What is included:

  • 7 Nights in double rooms in 3/4* hotels and agritourismi with breakfast
  • luggage transportation from hotel to hotel
  • Transfer Castelnuovo dell'Abate-Montalcino
  • Transfer Buonconvento-Monte Oliveto Maggiore,
  • Transfer Buonconvento-Monteroni and luggage to Siena
  • Maps and detailed description of the itinerary
  • 24h phone assistance
  • Medical-luggage insurance

What is not included:

  • Transfers to the starting location and from the arriving location of the tour
  • lunches and dinners, if not otherwise stated.
  • visits and entrance fees - tips
  • personal expense
  • possible sojourn taxes
  • everything that is not mentioned in the "What is included" section

Optional Services:

  • These services can be added to the ones included in the base price of the tour
  • Single room supplement
  • Transfers to reach the starting location or to leave the arriving location of the tour, which will be quoted on request.
Is this trip for me?

A trip to explore the iconic and beautiful Tuscan landscape - including places as famous as Montalcino, Siena, Pienza, and lesser known jewels such as Bagno Vignoni and Buonconvento. The Tuscan hills may result a bit challenging for beginners, but with a bit of preparatory training this trip is a suitable option for first-time hikers. 

S-Cape Countryside Travels srl
Borgo Allegri 16R
50122 Firenze FI
P. IVA 05227330486

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