val d'orcia hills and its path separated by cypresses
val d'orcia hills and its path separated by cypresses

Val d'Orcia, Montepulciano to Siena

79 km
8 days | 7 nights
Apr May Jun Jul Aug Sep Oct
price from
€ 911
CO2 footprint
95 Kg/person
  1. Italy
  2.  | 
  3. Self-Guided
  4.  | 
  5. Tourcode ITSW320

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. 


  • Visit the natural, artistic and cultural treasures of the Val d’Orcia, on the UNESCO heritage list;
  • Walk through streets of incredibly well preserved medieval and renaissance villages and hilltop towns;
  • Talk with friendly Tuscans and taste delicious regional culinary specialties;
  • Immerse yourself in quiet countryside paths and taste delicious tuscan specialities


Day 1

Arrive in Montepulciano

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

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

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

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

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

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

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

Depart from Siena

Last day included. Tour ends after breakfast. 


Is this 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. 


What is included:

  • 7 Nights in double rooms in 3/4* hotels and agritourismi with breakfast
  • luggage transportation from hotel to hotel (max 1 item per person)
  • Transfer Castelnuovo dell'Abate-Montalcino
  • Transfer Buonconvento-Monte Oliveto Maggiore,
  • Transfer Buonconvento-Monteroni and luggage to Siena
  • Maps and detailed description of the itinerary in digital form, app
  • 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.
  • travel documentation in printed form (maps and detailed description of the itinerary), shipped to the first hotel


We work with 3* hotels, B&Bs and farmhouses that reflect our way of experiencing travel: they are comfortable and characterful structures, which we choose one by one, managed by passionate and welcoming people.

Unless otherwise specified in the travel listing, all provide private en-suite rooms with breakfast included.

Below you see some examples of the facilities used for this trip, but keep in mind that they may vary based on availability in the period. We could therefore book for you structures different from those you see listed here, but of the same category and carefully chosen according to SloWays criteria.

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.

When to travel

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. 

What to bring

Clothing and other items
You will need your regular walking/cycling gear, including some sort of reflective garment. For the evenings, smart outdoor style trousers (or shorts) are invaluable, as are quick-dry t-shirts. These can be washed easily and will dry overnight and still look good for sightseeing or having a drink in town.

Take as little as possible to avoid potentially lugging a heavy suitcase up three flights of stairs at the end of the day. Please be aware that laundromats (“Laverie”) are not common in rural areas, so plan to do handwashing of small items.

Lightweight walking shoes/ trainers
For wearing around towns & villages. They can also be a back-up pair.

Socks & underwear
Take only good quality socks with quick-dry and insulating qualities. Road test them before you go on the trip. Take a suitable quantity of underwear as washing facilities are limited.

Warm jacket, hat, gloves
Bring a fleece, Polartec or warm layers for the evenings especially in spring or autumn; be sure it is totally suitable for your needs.
A fleece jacket which blocks the wind (Wind-stopper) is the most preferable. In the summer months a lightweight jacket is suitable for evenings.
If you are cycling/walking in mountainous or coastal areas, even in the height of summer, the weather can change very quickly and unexpectedly and you should be prepared for fog, mist, rain, snow or hail at any time. Always take an extra layer with you, as well as a warm hat and gloves.

Waterproof jacket & trousers
If you are caught in heavy rain, with good waterproof clothing you should remain dry. Remember that most garments will lose their properties over time. Few will remain waterproof for more than five years and many deteriorate in three years or less. We recommend a rain jacket with a good hood and collar and waterproof or thermal walking/cycling trousers or tights.

Dress code
In general, you should wear suitable clothing when entering a church (in many places, it is considered unacceptable to go inside wearing shorts or a tank-top). We suggest that women carry a shawl to cover up bear shoulders or low-cut tops. It also comes in handy when your shoulders get sunburned!

It is considered inappropriate for men to go without a shirt / T-shirt (other than at the beach).

Trekking poles (adjustable)
Highly recommended. A pair works best, depending on what you are comfortable with. If you suffer from back or knee pain this should be considered essential. Remember to practise walking with your pole(s) on different types of terrain in the months preceding your trip.

Walking boots
The importance of good footwear cannot be stressed enough. Your boots should be sturdy and of good enough quality to handle all types of terrain. Lightweight boots, (cordura/leather boots) which have Gore-Tex or sympatex water-proofing are most suitable for this trip. They should provide good ankle protection and be well broken in. Waxing leather boots regularly prolongs their life.

Walking tops & trousers
We recommend walking trousers and shorts and quick-dry wicking t-shirts. These can be washed easily and will dry overnight and still look good for sightseeing or having a drink in town. Wicking T-shirts are fast drying, keep moisture away from your skin and are available at outdoor stores. You should also bring one pair of loose-fitting trousers to wear in cities and for evenings out, etc. Shorts or zip-off trousers are useful in warmer weather.

Practical info

How to arrive

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

Mobile App

Use the SloWays APP for iOS and Android smart phones in combination with the written documentation provided.

The App has the detailed tracks and maps that you can use offline and without roaming. Thanks to the phone’s internal GPS, you can check your exact position on the map, so you always know exactly where you are. It also helps you self-navigate you way while travelling. More information on how to use the App inside the roadbook documents.

The navigation features include:

  • Offline navigation. Mobile data not required after initial download
  • Accurate GPS tracks
  • Autorotation of the maps
  • Daily route summary and elevation chart
  • Panorama of the track and at street level
  • Alarm and vibration that alerts you in case you go off track.
  • Emergency SMS button with position coordinates
  • Possibility to record and take georeferenced photos of problems on route alerting fellow travelers
  • Hotel information
  • Points of interest along the way
  • Historical background

Wanderlust Nominee Best Specialist Tour Operator 2023
Nominee Best Specialist Tour Operator 2023
Change currency:

We accept:


We accept:

FTO ATTA member
100% Green Travelife
FTO ATTA member 100% Green Travelife

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

© 2024 SloWays. All rights reserved.
Touroperating S-Cape Countryside Travels srl Borgo Allegri 16R 50122 Firenze FI, Italy
VAT Nr 05227330486

We and selected third parties use cookies or similar technologies for technical purposes and, with your consent, for functionality and marketing (personalised ads) as specified in the cookie policy. Denying consent may make related features unavailable.