A Taste of Tuscany Self-Guided Walking

Based in the town of Chianciano Terme, on this single-centre walking holiday you'll experience archetypal Tuscany: stunning timeless landscapes, delicious rustic cuisine, friendly local people and, of course, interesting walking routes.

A Taste of Tuscany Self-Guided Walking

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Trip Fee

$ 2.105

Date

28 March - 04 April 2026

Trip Information

This is not just a walking holiday it is a full immersion into local Tuscan life, from a guided walk passing the 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.

Activity Areas

Foodie Holidays
Self-Guided Walking
Walking & Trekking
Walking & Trekking
Walking & Trekking
Walking & Trekking
Walking & Trekking
Walking & Trekking
Walking & Trekking
Walking & Trekking
Walking & Trekking
Walking & Trekking
Walking & Trekking
Walking & Trekking
Walking & Trekking
Walking & Trekking
Walking & Trekking

Region & Country & City

Europe: Italy, Tuscany

Included in the Price


- All accommodation
- All buffet breakfasts and 4-course evening meals
- Management by local hotelier
- Headwater App
- Wine, olive oil and local produce tasting
- One thermal spa entrance

Not Included In The Price


- Travel insurance
- Visas or vaccinations
- Arrival & departure transfers for land only bookings (available on request and at a supplement)
- Single accommodation (available on request)  - compulsory supplement

Accommodation Information


- 7 nights single-centre accommodation in a HHH hotel
- Management by local hotelier
- Route directions and maps

Map

Itinerary

Day 1 Arrive in Chianciano Terme

Arrive at the Agriturismo La Pietriccia and enjoy a stroll to the old town, before your evening briefing by the owner, Stefano, and the first of many home cooked dinners. (Staying at the Agriturismo La Pietriccia for 7 nights, Half Board)

Day 2 Chianciano circular walk

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

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

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 argiturismo 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

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

After a short transfer to Pienza, take time to explore the town, it is one of the cheese capitals of Italy, and a beautiful mediaeval 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 mediaeval 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

Travel Dates

28 March - 04 April 2026 $ 2.105

04 - 11 April 2026 $ 2.105

11 - 18 April 2026 $ 2.105

18 - 25 April 2026 $ 2.105

25 April - 02 May 2026 $ 2.105

02 - 09 May 2026 $ 2.300

09 - 16 May 2026 $ 2.300

16 - 23 May 2026 $ 2.300

23 - 30 May 2026 $ 2.300

30 May - 06 June 2026 $ 2.300

06 - 13 June 2026 $ 2.300

07 - 14 June 2026 $ 2.340

13 - 20 June 2026 $ 2.300

20 - 27 June 2026 $ 2.300

27 June - 04 July 2026 $ 2.300

04 - 11 July 2026 $ 2.105

11 - 18 July 2026 $ 2.105

18 - 25 July 2026 $ 2.105

25 July - 01 August 2026 $ 2.105

01 - 08 August 2026 $ 2.105

08 - 15 August 2026 $ 2.105

15 - 22 August 2026 $ 2.105

22 - 29 August 2026 $ 2.105

29 August - 05 September 2026 $ 2.105

05 - 12 September 2026 $ 2.300

12 - 19 September 2026 $ 2.300

19 - 26 September 2026 $ 2.300

26 September - 03 October 2026 $ 2.300

03 - 10 October 2026 $ 2.300

10 - 17 October 2026 $ 2.300

17 - 24 October 2026 $ 2.300

27 March - 03 April 2027 $ 2.225

03 - 10 April 2027 $ 2.225

10 - 17 April 2027 $ 2.225

17 - 24 April 2027 $ 2.225

24 April - 01 May 2027 $ 2.225

01 - 08 May 2027 $ 2.435

08 - 15 May 2027 $ 2.435

15 - 22 May 2027 $ 2.435

22 - 29 May 2027 $ 2.435

29 May - 05 June 2027 $ 2.435

05 - 12 June 2027 $ 2.435

12 - 19 June 2027 $ 2.435

19 - 26 June 2027 $ 2.435

26 June - 03 July 2027 $ 2.435

03 - 10 July 2027 $ 2.225

10 - 17 July 2027 $ 2.225

17 - 24 July 2027 $ 2.225

24 - 31 July 2027 $ 2.225

31 July - 07 August 2027 $ 2.225

07 - 14 August 2027 $ 2.225

14 - 21 August 2027 $ 2.225

21 - 28 August 2027 $ 2.225

28 August - 04 September 2027 $ 2.225

04 - 11 September 2027 $ 2.435

11 - 18 September 2027 $ 2.435

18 - 25 September 2027 $ 2.435

25 September - 02 October 2027 $ 2.435

02 - 09 October 2027 $ 2.435

09 - 16 October 2027 $ 2.435

16 - 23 October 2027 $ 2.435

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