A Taste of Tuscany Walking

  • Overview
  • Itinerary
  • Dates
  • Headwater

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

Agriturismo la Pietriccia (3 star)
The Agriturismo Pietriccia is a wonderful place sitting across a small valley from the old town of Chianciano, rewarding you with wonderful views. The simple hotel has large rooms with 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 a small garden area with a shady area. The food is superb traditional cuisine, and 65% of the produce is grown or reared on site.

British Airways Heathrow to Rome Fiumicino 07:30/10:30 then rail Rome Termini to Chiusi 13:00/14:49 and transfer to hotel 25 minutes. Return: Transfer to Chiusi station 25 minutes then rail Chiusi to Rome Termini 10:54/12:48 then British Airways Rome Fiumicino to Heathrow 17:25/19:05.
All buffet breakfasts and 4-course evening meals
Single Supplement
48 per night for sole occupancy of a double room
  • Italy
  • Tuscany
  • Europe
Tour Types
  • Self Guided
  • Walking
Departure Points
  • London Airport
Day 1: Arrive in Chianciano Terme
Take the train from Rome to Chiusi-Chianciano, where you will be met and transferred to your hotel. Perhaps enjoy a stroll to the old town, before your evening briefing by the owner, Stefano, and the first of many superb dinners.

Day 2: Visit the farms 12-13km/7.5-8mi/4-5hr
You'll start this morning with a guided walk passing the different producers that make this a special part of the world, through fruit orchards and vineyards, starting at a local oil mill, then visiting the Cinta Senese pigs followed by an area set up to allow truffles to grow and finishing off in Chianciano Vecchia, with great views of the Valdichiana before enjoying wine and local produce tasting in a charming cantina in the old town.

Day 3: Castiglioncello to the hotel 13km/8mi/4.5hr
A short transfer takes you to the charming village of Castiglioncello; once abandoned it is now restored with a hotel and 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, follow a path downhill through the forest to reach the beautiful Villa la Foce, the former residence of the noble Origo family and enjoy a drink at the Dopolavoro La Foce before a transfer back to the agriturismo.

Day 4: A Walk to Lake Chiusi 14km/8.8mi/4.5hr
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 5: Afternoon cookery course
This morning you have time to yourself, maybe walk into Chianciano Vecchia and visit the Etruscan Museum of Chianciano Terme, or use your voucher for the Theia Spa and relax in the healing waters or treat yourself to one of their many treatments. In the afternoon you begin your cookery class where you will learn classic Italian techniques and eat the meal you prepare for dinner.

Day 6: Walk to the wine town of Montepulciano 15km/9.5mi/5hr
A short transfer out of Chianciano to start the 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, then detour to the Convento dei Cappucini (optional), 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/7mi/3.5hr
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 da 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 superb food.

Day 8: Leave Chianciano Terme
We take you back to the train station where you could possibly head to Florence or Rome for extra nights.

You will have the option to book your own flights independently with the operator.

Dates Price Single Availability
24-Aug-2019 for 7 Nights Visit Website
24-Aug-2019 for 7 Nights Flight Included Visit Website
31-Aug-2019 for 7 Nights Visit Website
31-Aug-2019 for 7 Nights Flight Included Visit Website
07-Sep-2019 for 7 Nights Visit Website
07-Sep-2019 for 7 Nights Flight Included Visit Website
14-Sep-2019 for 7 Nights Visit Website
14-Sep-2019 for 7 Nights Flight Included Visit Website
21-Sep-2019 for 7 Nights Visit Website
21-Sep-2019 for 7 Nights Flight Included Visit Website
28-Sep-2019 for 7 Nights Visit Website
28-Sep-2019 for 7 Nights Flight Included Visit Website
05-Oct-2019 for 7 Nights Visit Website
05-Oct-2019 for 7 Nights Flight Included Visit Website
12-Oct-2019 for 7 Nights Visit Website
12-Oct-2019 for 7 Nights Flight Included Visit Website
19-Oct-2019 for 7 Nights Visit Website
19-Oct-2019 for 7 Nights Flight Included Visit Website
26-Oct-2019 for 7 Nights Visit Website
26-Oct-2019 for 7 Nights Flight Included Visit Website

Touring with Headwater

In 1985, Richard and Christine Bass made the life-changing decision to turn a passion into a business and thus Headwater was born at their kitchen table.

The first Headwater tours were launched in summer 1986 and modestly comprised three holidays in the Upper Loire Valley in France: a canoeing holiday and two self-guided walking holidays.

Their vision for Headwater was clear, right from the start. Richard and Christine wanted to offer their customers exactly what they loved in a holiday – family-run, friendly hotels, an authentic experience of a region, including culture, cuisine and fine wines, and above all a fantastic level of personal service, with staff on hand in resort to help and guide as required.

After a successful 10 years specialising in France, Headwater launched a new Great Walks in Europe brochure in 1995, offering a selection of hand-picked guided walking holidays in eight countries. As a result of the phenomenal success of this, a year later the first self-guided walking and cycling holidays in Italy were launched.

In 1999, Richard and Christine decided to retire and enjoy the fruits of their labour, and sold Headwater – but not before ensuring it was in the safest of hands to continue their legacy.

Today, they enjoy taking customers (new and loyal) on journeys on foot or by bike throughout 18 countries worldwide. Whilst they have embraced modern technology and changing times since 1985, Richard and Christine’s ethos remains key to all of their holidays and they consider it their mission to ensure that the same detail, knowledge and passion goes into delivering each and every trip.

With more than 32 years’ experience, their collection now includes 59 self-guided and 12 guided walking holidays and 62 cycling holidays. Their canoeing holiday in the Dordogne remains as popular as ever, as well as their choice of winter snow holidays (cross-country skiing and winter walking) that run between December and April in Austria and Norway.

They are particularly proud of their Headwater-employed representatives (reps) who are on-hand in 15 regions in France, Italy, Spain, Portugal, Austria and Bavaria. Burgundy is their longest-standing “repped region” – Richard and Christine researched the holidays and they have been running them since 1992. Their reps provide 24-hour support in resort including: briefing you on arrival, transporting your luggage from hotel to hotel, offering a ‘Wine Service’ where they collect any bottles you’ve purchased en route and transport them to your final hotel for you, and giving you tips and advice and sharing their knowledge of the local area, the routes, the best views and generally helping you to make the most of your trip. Each year, before the season starts, the reps have an in-depth training session at Headwater HQ to make sure they’re ready for the summer ahead.

Their newest addition to the Headwater portfolio is a selection of single-centre activity holidays in Brittany and the Dordogne, France and Catalunya, Spain. These are ideal for multi-generational families and groups – take a look below for some Headwater inspiration.


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