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Italy: Tuscany

A Taste of Tuscany Walking

Trip code: W07ST

Average customer rating 4.9 / 5(33 verified reviews)

Self-Guided Walking
7 nights single centre
Moderate
COโ‚‚ rating 1/5
Headwater Navigation app

Trip highlights

Fabulous insight into traditional Tuscan life: the food, the wine, the culture

Wonderfully varied walking, including the beautiful UNESCO Val dโ€™Orcia

Delicious classic Tuscan cuisine โ€˜km 0โ€™ cooking (all local food)

The wine and cheese towns of Montepulciano and Pienza

Warm and welcoming agriturismo (farmhouse accommodation) with a passionate owner โ€“ the best of Italian hospitality

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Trip details

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. Youโ€™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.

What's included

Included

  • 7 nights in 3-star equivalent accommodation
  • All breakfasts and all evening meals
  • Briefing at the start of your holiday
  • Headwater navigation app
  • Wine, olive oil and local produce tasting
  • 1 thermal spa entrance

Not included

  • Flights
  • Local taxes/fees
  • Travel insurance

Travel options

Our travel specialists can arrange flights, rail and transfers to this holiday from wherever you are. Call us to plan your journey. +44 1606 720099

Itinerary

Route map, with each night's stop marked
The full route, night by night. Select the map to view it full screen.

Day 1 ยท โ€”Arrive in Chianciano Terme

Arrive in Chianciano Terme

Arrive at the Agriturismo La Pietriccia. In the evening, thereโ€™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

Pool and view at La Pietriccia
equivalent

Agriturismo la Pietriccia

Chianciano Terme

  • Air conditioning
  • Diners Club
  • Hairdryers
  • Mastercard
  • Other email access
  • Safe
  • Swimming pool
  • Tea & coffee
  • Television
  • Visa cards

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 agriturismoโ€™s apartments, these are located 100m from the main agriturismo.

Day 2 ยท 13km/8.1miChianciano circular walk

Chianciano circular walk

Todayโ€™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 Chiancianoโ€™s medieval centre, from where you can make your way back to the hotel or spend more time exploring this ancient spa town.

Elevation

Chianciano circular walk elevation profile

Day 3 ยท 14km/8.7miA Walk to Lake Chiusi

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.

Elevation

A Walk to Lake Chiusi elevation profile

Day 4 ยท 9km/5.6mi or 19km/11.8miCastiglioncello to the hotel

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 dโ€™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.

Elevation

Castiglioncello to the hotel elevation profile

Day 5 ยท โ€”Free day

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 ยท 17km/10.6miWalk to the wine town of Montepulciano

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.

Elevation

Walk to the wine town of Montepulciano elevation profile

Day 7 ยท 11km/6.8miPienza to Bagno Vignoni

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 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 dโ€™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 Stefanoโ€™s lovely food.

Elevation

Pienza to Bagno Vignoni elevation profile

Day 8 ยท โ€”Leave Chianciano Terme

Leave Chianciano Terme

Leave Chianciano Terme.

Extending your holiday

Exterior of the Hotel Canada Roma

Hotel Canada Roma

Rome

  • Air conditioning
  • American Express
  • ATM
  • Bank
  • Hairdryers
  • Market
  • Mastercard
  • Safe
  • Shops
  • Tea & coffee

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.

What our travellers say

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 deliciousโ€ฆ.in fact we had to ask for small portions as we couldnโ€™t keep up with the four courses!
A great holiday!

Ms Dacie

An experience to treasure. Learned about the people and the area; enjoyed seeing how the farm was organised and how the โ€˜slow foodโ€™/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

Stephano was a wonderful host, couldnโ€™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

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. Couldnโ€™t have been better.

Mr Munden

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

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

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

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

Mr Macleod

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

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 itโ€™s not raining!

Mr Smith
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Positive impact

Carbon score for this trip

15.0

Kg COโ‚‚e

per person, per night

Relative to other Headwater trips

We measure emissions from the parts of the holiday we organise โ€” including accommodation, in-trip transport, meals and activities โ€” and express them as COโ‚‚e per person, per night. Our label doesnโ€™t include your travel to and from the start of the trip. As a Certified B Corp, Headwater is committed to reducing this figure and to positively impacting local communities, the local environment and our staff. Learn more

Fromยฃ1,289per person