Italy : Tuscany

A Taste of Tuscany Walking

Trip code: W07ST 4.9 (27 reviews)

Self-guided walking

7 nights,
single centre

Level: 2

15.0Kg CO2e

Navigation App


  • Fabulous insight into traditional Tuscan life: the food, the wine, the culture
  • Wonderfully varied walking, including the beautiful UNESCO Val d'Orcia
  • Delicious classic Tuscan cuisine 'km 0' cooking (all local food)
  • The wine and cheese towns of Montepulciano and Pienza
  • Warm and welcoming agriturismo (farmhouse accommodation) with a passionate owner - the best of Italian hospitality


  • 7 nights accommodation
  • All breakfasts and 4-course evening meals
  • Briefing at the start of your holiday
  • Headwater navigation app
  • Wine, olive oil and local produce tasting
  • 1 thermal spa entrance


This is not just a walking holiday it is a full immersion into local Tuscan life, from meeting local produce providers to wine-tasting, and a chance to bathe in sulphur-rich healing waters. You'll walk through ancient chestnut forests, vineyards and olive groves, passing lakes and freshwater ponds alive with the sounds of frog chorus. Visit medieval, Roman and Etruscan towns and villages, sample the Vino Nobile of Montepulciano, rich Pecorino cheese in Pienza or take a bath in Roman Bagno Vignoni.




Day 1: Arrive in Chianciano Terme

Arrive at the Agriturismo La Pietriccia. In the evening, there's a briefing by the owner, Stefano, and then the first of many home cooked dinners. (Staying at the Agriturismo La Pietriccia for 7 nights, Half Board)

You stay at Agriturismo la Pietriccia.

hotel details

 equivalent

Agriturismo la Pietriccia, Chianciano Terme



The Agriturismo La Pietriccia is a wonderful place sitting across a small valley from the old town of Chianciano, rewarding you with wonderful views. The large rooms have a simple, rustic decor and some offer balconies or terraces. You will be given a warm welcome by the owner Stefano, who is extremely passionate about the produce of the local area and the nature.
The agriturismo has a lovely pool and terrace; there is also a shady garden area where in warm summer weather, you can relax reading a book. The food prepared by Stefano, his brother Simone and Katia, is cooked using the mainly organic produce grown or reared on site or by one of the local producers offering traditional Tuscan cuisine at its best.
Please note that if you have booked one of the agriturismo's apartments, these are located 100m from the main agriturismo.

Day 2: Chianciano circular walk (13km/8.1mi)

Today's walk takes you over the hills around la Pietriccia, with stunning views over Monte Marzolana and Chianciano Terme itself. The walk will finish in Chianciano's medieval centre, from where you can make your way back to the hotel or spend more time exploring this ancient spa town.

Day 3: A Walk to Lake Chiusi (14km/8.7mi)

As you descend into the Valdichiana, a mix of quiet lanes and gravel tracks provide perfect views of the vineyards and over to Monte Rufeno. Passing pretty farmhouses you make your way to the small town of Montallese, and from here you pick up the Sentiero della Bonifica, a long-distance path between Chiusi and Arezzo. This leads you to the charming Lake Chiusi, where you can enjoy the birdlife and perhaps lunch at the lakeside restaurant. You will be transferred back to the hotel.

Day 4: Castiglioncello to the hotel (9km/5.6mi or 19km/11.8mi)

A short transfer takes you to the charming village of Castiglioncello; once abandoned it is now restored with a hotel, a cafe and the interesting Etruscan burial site. From the village you follow a trail through the forest to pass wonderful viewpoints of the area, dropping down to Poggio Pietraporciana, a Nazi gun point in the war. Continuing through the Pietraporciana Nature Reserve you pass the Rifugio Pietraporciana, once owned by the Marchesa of Val d'Orcia, Iris Origo, who, during the war, cordoned off this area to create a neutral zone, which the allies, Nazis and partisans all obeyed. From here, a forest track takes you past a charming agriturismo before a trail along a dried up river alongside rocky cliffs and on to the outskirts of Chianchiano stopping at the Dopolavoro La Foce where an optional transfer back to the hotel awaits you. Alternative carry on walking along a narrow trail with wonderful views and past a model of an Etruscan farm, before arriving in Chianchiano Terme and a choice of following the white gravel roads passing farms or through the town to return to the agriturismo.

Day 5: Free day

Today you have time to yourself, maybe walk into Chianciano Vecchia and visit the Etruscan Museum of Chianciano Terme, enjoy olive oil tasting at the agriturismo or use your voucher for the Thermal Spa and relax in the healing waters or treat yourself to one of their many treatments.

Day 6: Walk to the wine town of Montepulciano (17km/10.6mi)

Today you walk to the wine town of Montepulciano, where you will be rewarded with stunning views across the Valdichiana. Follow a chestnut-laden track to meet the forest road, before following a track around the vines and farmlands up to Montepulciano. You will be picked up here, but before this, take time to explore the town, which is full of wine bars and shops and has plenty of tasting opportunities.

Day 7: Pienza to Bagno Vignoni (11km/6.8mi)

After a short transfer to Pienza, take time to explore the town, it is one of the cheese capitals of Italy and a beautiful medieval historic centre. Perhaps pick up a sandwich filled with porchetta or a slab of rich and creamy pecorino cheese. The walk takes you downhill from Pienza, crossing the stunning Val d'Orcia. It is an easy walk following a well-marked trail, giving you the chance to take in the views of medieval towns, rolling hills and rows of cypress trees. You will reach Bagno Vignoni then follow the river Orcia before climbing up to the town passing the spring baths and the old mill, before arriving in the Roman town, with its large baths in the centre of town. Perhaps treat yourself to the hot waters of the Hotel Posta Marcucci, where the baths come with a view! We transfer you back to the hotel for your final night of Stefano's lovely food.

Day 8: Leave Chianciano Terme

Leave Chianciano Terme.

Extending your holiday

If you'd like to extend your trip with extra hotel nights we recommend: Hotel Canada Roma, Rome.

hotel details


Hotel Canada Roma, Rome


Cash machine

The 3 star Hotel Canada Roma is centrally located near the main railway station, making it an excellent base from which to explore Rome. Each room is ensuite and has been lovingly decorated in an elegant Italian style complete with vintage furniture. Rooms come with tea and coffee maker as well as air conditioning and safe.
This well appointed hotel also boasts a bar for pre dinner drinks and nibbles, as well as an external courtyard where you can savour a drink under the stars.

Room upgrades: Deluxe and junior suite
Deluxe rooms are larger with a more stately decor.
Junior suites have a separate living room.



These tour only prices are based on two people sharing. Single supplement from $441.

These flight inclusive prices are based on two people sharing. Single supplement from $441.

  • Alternative flights, including regional departures
  • City-break add-on in Rome
  • Single occupancy
  • Travel options and Transfers

Call now to speak to our specialist team at 0044 1606 720199 or email us at for enquiries or to book your trip.


Christine and I have a walking holiday each year and we always travel with Headwater because of the reliability of the quality of service and assistance if and when required.

Barbara Philliben, 15 Apr 2024


It’s not our favourite walking holiday with Headwater, because at time the Strada Blanche seemed to drag on. We prefer walking in woodland, such as in Alsace Vosges or the French Jura. I think this holiday is more suited to cycling - we saw many happy cyclists out there.

However Stefano is definitely one of the best hosts we’ve had, such fun and passion. La Pietriccia is a great location too, with lovely food and service.

Andrew Asteriades, 16 Sep 2023


Thoroughly enjoyed this holiday. Walks were long but manageable through stunning tuscan countryside. You will need to have a portable charger for your phone in order to use the app as it uses up battery life quickly. The accommodation was good, spacious rooms clean and comfortable. The staff were helpful, efficient and welcoming. The food was very good filling and tasty. Local wine was very pleasant. On the free day the spa was very enjoyable. There is a long train journey to contend with which was a slight drawback. However, I would highly recommend this holiday if you like long self-guided walks through stunning countryside, comfortable accommodation, good food and wine, expertly organised by Headwater.

Gwilym Edwards, 9 Sep 2023


We thought Tuscany was great and so was the whole holiday. We are all getting on a bit average age 77 and Stephano helped us shorten the walks. We loved the hotel, always too much food and the local wine great and excellent value. Swimming pool just what was required and used every day. Owner great fun and very helpful. Four of us had 3 extra days and he helped us hire a car locally. All the staff were very helpful. The extra days were used to visit Siena and Pienza and were well worth it.

Roger Bishop, 2 Sep 2023


Fully up to expectations. our host provided us with an app called Ride with GPS for our phones. The routes were marked and easy to follow in real time except that we were caught out by a failing battery power.It might be good to remined future clients that it is worth having a reserve battery power pack to top up the phone if they want to use this facility. Howevere the written instructions you gave us were very good.

HANCOCK, 20 May 2023


A full days journey to get there and return home which is tiring particularly as the service on arrival at Rome Airport was bad and rude.

Once at Chiancino it was a delight

CAMERON, 20 May 2023


All that we were looking for in this holiday - great location, stunning scenery, peace when walking, great support and excellent food - the first proper holiday for one of us in a long while and well overdue.

The only note is, wow, Tuscan food can be rich/heavy!! Used to more of the Mediterranean style Italian food and occasionally it was a bit too much for both of us in the meat and/or cheese combinations. But always excellent in taste and quality which really shone through.

Stefano and the team were outstanding, very helpful and knowledgeable. He's a great host and ambassador for you and the rest of the team were also very kind and helpful. Location is perfect, the walks measured and always end in somewhere nice for a late lunch and wander in some shady streets. Mid September was a great time - not too hot or crowded but still plenty going on.

Mr Tebbutt, 10 Sep 2022


La Peitriccia is a delightful agriturismo. The family were charming and Stefano could not do enough for us. We had a meeting with him every day after breakfast when he helped us work out what we wanted to do. We were a group of four, all over the age of 69! We did find the walks a bit too much for us but Stefano adjusted them and drove us to destinations and collected us when we finished the walks. The rooms were simple but very adequate and we had a lovely terrace looking over vineyards and up to the hill top village, where we had an interesting delicious wine tasting following our first day's walk.

The meals were excellent. They were always cooked freshly using local produce. There was no choice but this did not prove a problem and they felt very authentic. We drank the local wines which were delicious. The swimming pool was not heated but was very pleasant although we didn't have that much time to use it. Highly recommended.

Mrs Marris, 20 Aug 2022


Stephano offers an authentic Italian experience which is all about his organic farm and what he produces, and the countryside and birds that he knows intimately and which he loves. Stephano (and his brother) welcomed us and did everything to ensure we had a good experience, we thoroughly enjoyed them and their offer. The food was prepared with care/attention to its health benefits and food miles. We loved the Tuscan countryside which you see so well by foot although it was extremely hot by midday so walks had to be undertaken earlier in the day, and some were shortened to avoid the heat. This was an unusual level of heat for June. The only difficulties we had with travel was when we returned to Heathrow, otherwise tickets and travel arrangements were excellent. Our holiday was post Covid when the hospitality industry is under pressure, we were therefore not able to have the Cookery session. Thoroughly recommend the Theia Spa and massage which had to be booked ahead.

Mr Ball, 11 Jun 2022


This part of Tuscany is beautiful and the hill top towns and villages are delightful. The agro tourism accommodation is a pleasant change from a standard hotel. It is lovely to be surrounded by olive trees and vines.

The food was of a very high standard, but as someone who eats little meat, I opted not to eat some of the main courses. We thoroughly enjoyed all of the walks, although the temperature was 8 deg C warmer than is usual for mid May. There are many wonderful photo opportunities. On the free day we enjoyed a visit to the thermal baths and a well deserved massage. I would encourage others to do this holiday and it was very good value for money. The only down side is the two trains and taxi journey each way to and from Rome airport, but it is ultimately worth it to reach your final destination.

Dr Horne, 14 May 2022


A lovely holiday with congenial fellow guests in a beautiful location. Stefano is a welcoming and enthusiastic host, and endeavours to be flexible to his guests' needs and wishes. We would recommend going when it is not as hot - late September or May would be perfect. Our favourite walk was from Castiglioncello del Trinore, through the forest, and we recommend visiting the thermal baths, and paying extra for the spa and the 'emotional showers'!

Ms Kinder, 31 Aug 2019


This was a fabulous experience - the food, views and staff were all wonderful

Mrs Hinchliffe, 3 Aug 2019


The location for a walking holiday was excellent. Stefano and Family provide a most welcoming atmosphere for all aspects of your holiday. Stefano provided excellent route guidance, modifications and recommendations. Stefano's passion for local produce and good healthy eating is reflected in a diverse daily menu, which is both very enjoyable and adaptable. This was our first visit to Tuscany, we would highlight recommend this holiday and would most definitely visit again.

Mr Wood, 20 Jul 2019


Excellent holiday that worked really well mainly to the efforts that Stefano has put in to ensure that routes are easy to follow with his electronic guide and the friendliness and helpfullness of his staff and family.

Mrs Davies, 29 Jun 2019


Enjoyable holiday through beautiful scenery. Stephano and his family could not have been more helpful and friendly

Ms O'Kelly, 8 Jun 2019


The host Stephano was brilliant in all respects. The breakfast was limited in choice. Evening meal was traditional to the area. Accommodation was a bit basic . Walking was excellent and was able to be adapted to people’s needs. The extras were a treat, eg spa visit, cookery lesson and olive oil lecture.

Mrs Berry, 1 Jun 2019


Excellent holiday which more than met our expectations. Stefano went over and above to make us feel welcome and give accurate and useful information about our walks. The cooking and spa were fun alternatives to walking each day.

Mrs Newman, 11 May 2019


Stefano and his staff at La Pietriccia did everything to make our holiday successful. We got what we expected, and more! A return trip is called for, but when it's not raining!

Mr Smith, 27 Oct 2018


Another excellent trip with Headwater, this time to a splendid Agriturismo in Tuscany, with excellent facilities, a great location for walking and superb cooking. Additional features included a cooking lesson one afternoon, a spa visit and a very enjoyable wine/cheese/salumi tasting in town. Thanks to Stefano and his family and friends for a very warm welcome and a most entertaining time!

Mr Christy, 13 Oct 2018


Excellent holiday, food fantastic and Stefano was so enthusiastic about his cooking and the environment

Mr Macleod, 22 Sep 2018


This holiday was a great way to enjoy the Tuscan landscape, food, wine and local people. Really enjoyed the local countryside, villages and towns and came away feeling relaxed, well fed and keen to visit the area again.

Ms Findlay, 15 Sep 2018


This was a wonderful experience of rural Tuscany in a delightful Agriturismo with fantastic food and staff who made you feel very welcome. Stefano was very helpful in organising our walks and tailoring them to suit all abilities. This was one of our best holidays and we would really recommend this lovely corner of Tuscany.

Mr Reeves, 8 Sep 2018


Flexibility of walks during the week was a real positive. Hot days were catered for by Stefano and option to not walk at all was great. Additional Wine tasting, cooking and Spa gave good variety as well

Mr Lovell, 8 Sep 2018


A glorious experience of real rural Tuscany in every way. The staff made you feel part of the family and Stefano in particular made sure every aspect of the holiday was tailor made for each person. Couldn't have been better.

Mr Munden, 8 Sep 2018


Stephano was a wonderful host, couldn't be more welcoming or helpful and we had a wonderful Tuscany experience. Had time to soak up the wild flowers , butterflies and wonderful aroma of the countryside.

Mrs Paton, 26 May 2018


An experience to treasure. Learned about the people and the area; enjoyed seeing how the farm was organised and how the 'slow food'/organic methods benefit the community.

Fantastic local produce including the wines. Walking routes were challenging but offered a real sense of achievement. Such a beautiful, sensuous region. Did not want to leave!

Ms Earl, 12 May 2018


Stephano was an enthusiastic host and made us feel very welcome. He was very keen to please as were the other members of his family who are involved in the farm enterprise. He shared his passion for the region and for local living, telling us all about olive oil, bee keeping and wine making amongst other things and we learned a lot! The walking was excellent and the food was very plentiful and fact we had to ask for small portions as we couldn’t keep up with the four courses!

A great holiday!

Ms Dacie, 5 May 2018


Self-guided walking

7 nights,
single centre

Level: 2

15.0Kg CO2e

Navigation App

7 nights from $2675


Call: +44 1606 720199