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Traveller Rating


  • self guided walk
  • 7 nights 3 or 4 star hotels and agriturismo
  • 7 Breakfasts

8 Days£1130GBP


Trip Code: JTM

Trip highlights

  • Medieval villages & hilltop towns
  • Regional culinary specialities
  • Cypress lined hills & vineyards

The Tuscan landscape of the Val d’Orcia will open your eyes to its natural beauty. This walk takes you along steep valleys, dense forests, rivers and the legendary “badlands” eroded clay slopes. Walk by quintessential farmhouses nestled amidst olive groves, vineyards and fig trees on your way to the hot spring hamlet of Bagno Vignoni and the Renaissance city of Pienza. On this week long exploration, you will visit palaces, Romanesque churches, thermal baths, and wineries serving the divine local red “Brunello”.



Starting Point:


Finishing Point:


Make your own way to Montepulciano. Standing high atop a hill in southern Tuscany, Montepulciano is a medieval town full of elegant Renaissance palaces, ancient churches, charming squares and hidden corners. It boasts vast panoramas all over the wonderful Val d'Orcia and Val di Chiana valleys that surround it.

Meals:  Nil

Starting from the San Biagio Church you follow a quiet track to the peaceful village of Montichiello where you can stop 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; a great spot to indulge in Tuscan treats!

Meals:  B

Today you wander through rolling hills, oak woods, cypress trees and pretty villages. From the start of the walk you will have views across the valley. Descend before climbing up to the town of San Quirico d' Orcia, a walled city with a 12th century church. Make your way to the village of Bagno Vignoni with its thermal hot springs.

Meals:  B

You will be transferred from Bagno Vignoni to Castelnuovo dell'Abate. As you arrive in the village, you will enjoy the stunning beauty of Sant'Antimo Abbey, a former Benedectine monastery dating back to the 8th century A.C. The first section of the walk to Montalcino will bring you to some panoramic views overlooking the beautiful Orcia Valley. Prepare for some exquisite local wines as you arrive in Montalcino.

Meals:  B

A hearty breakfast will set you up for an enjoyable 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. Depending on accomodation booked, you will either spend two nights in Pieve a Salti or Buonconvento.

Meals:  B

After breakfast transfer to the monastery at Monte Oliveto Maggiore. Begin your walk at the watchtower and make your way to the little village of Chiusure. Pass farmhouses along the way and once more this walk provides great views of the Crete Senesi landscapes.

Meals:  B

Today you will start with a short transfer to Monteroni d’Arbia from where you start the walk towards Siena. Hike through a landscape of rolling hills and small hamlets as the unmistakable sight of Siena appears in the distance. Once you reach Arbia train station take the train into Siena. Option to pre-book a vehicle transfer. Enjoy the magnificent beauty of Siena, famous for its biannual “Palio” horse race, held in the most beautiful shell-shaped square in Europe: the Piazza del Campo. Don’t miss a visit to the Duomo, an architectural treasure, and numerous imposing medieval palaces.

Meals:  B

After breakfast, make your way to the train station for your onward journey or book an extra night to spead more time exploring this wonderful city.

Meals:  B



The map and elevation chart are for illustrative purposes only and meant to provide general guidelines.
On self guided trips, actual route information provided before departure will be more detailed.


  • 7 breakfasts
  • 7 nights in 3-4 star hotels & agriturismo
  • Vehicle transfers day 4,6 & 7
  • Luggage transfer (1 bag per person not weighing anymore than 20kg)
  • Digital information pack: navigational App (can be used offline) with route notes & maps. Smartphone essential
  • Emergency hotline

  • evening meals, all lunches & beverages
  • Entrance fees
  • Travel insurance
  • Travel to the start and from the end point of the trip
  • Personal expenses such as laundry and phone calls
  • Tourist taxes
  • A supplement will apply if you are travelling solo or book a single room
  • Guide - this is a self guided holiday




Introductory to Moderate. There are nonetheless some steep and quite long hills, some fairly steep but short descents and some paths with rough gravel, stony and occasionally muddy surfaces. Fitness: High standard of fitness is not necessary but clients should be able to walk for up to 7 hours a day in hot sun on dusty or stony tracks.

Departure dates

Daily 01 Apr to 31 Oct


Black out periods: 24-26 Jun & 9-10 Aug due to Palio Horse Races in Siena

Priceper person from


Options & Supplements*
  • Single Room SupplementGBP£240
  • Solo Traveller SupplementGBP£510
*Prices listed are per person

Trip reviews

Why travel with us

Personal Experience

We've been walking and cycling the planet for over four decades and are passionate about delivering exceptional service. Combined, we’ve travelled to virtually every corner of Europe, and are eager to share the many benefits of travelling on foot or by bike.

Great Value & Quality

Our well priced trips offer great value for money. Included in your package are comprehensive route notes, maps & guide books along with bag transfers and locally run accommodation. We take the stress out of organising your holiday.

Self-Guided Specialists

We have been operating active self guided holidays since 1973. We handle all the necessary logistics so that you can relax and explore your destination at your own pace. Many of our tours depart daily, giving you even greater flexibility.