A Taste of Tuscany Cycling

  • Overview
  • Itinerary
  • Dates
  • Headwater

This single-centre cycling holiday introduces you to quintessential Tuscany; it has all the ingredients to create a wonderful lasting impression of this rightly famous region: the landscapes, the food, the people and, of course, perfect cycling routes.This is not just a cycling holiday it is an immersion into local Tuscan life.

Single Supplement
48 per night for sole occupancy of a double room
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.
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.

All buffet breakfasts and 4-course evening meals
  • Europe
  • Tuscany
  • The Bay of Naples
  • Italy
Tour Types
  • Cycling
  • Self Guided
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 and the first of many superb dinners.

Day 2: The Lakes Circuit 41km/25mi
A gentle start to the week with a lovely descent from your hotel on quiet roads, with wonderful views across to the mountains. A forest tracks leads you to the small town of Montallese and on to Lake Chiusi. Enjoy lunch at the lake then take the Sentiero Della Bonifica, a long-distance path between Chiusi and Arezzo, to the small Lake Montepulciano. This is a nature reserve teeming with birdlife, and there is also a cafe to enjoy a refreshment. Returning to the agriturismo you climb on tarmac road passing vineyards for as far as the eye can see, before an undulating track leads you back to your hotel.

Day 3: Radicofani 34km/21mi
The leg work is done for you this morning as we transfer you to Radicofani, the highest point in the Val d'Orcia - the views are incredible, be sure to take time to walk up to the highest point of the castle. Then follow the road downhill for the next 10 kilometres down into the valley. A gravel track takes you past pretty farms and through the forest to pass the beautiful private gardens of La Foce, before an up and over and down to the Agriturismo. You'll enjoy a spot of wine- tasting this evening before dinner in a beautiful cantina in the old town.

Day 4: Sarteano Loop 39km/24mi
Descending from the agriturismo you follow country tracks passing a truffle-growing area before a boulevard of olive trees takes you to a lovely trail crossing the Astrone stream. Continue cycling along a road with beautiful views of the valleys which takes you into mediaeval Sarteano: here you circle the walls and can enjoy a coffee before you carry on to Cetona. A narrow tarmac road takes you up this town, before a climb to Mondo X, where one of the best restaurants in Italy, La Frateria, is housed inside a beautiful convent started by St Francis in 1212. An extraordinary priest uses the monastery as a rehabilitation centre for troubled youths. From here had 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: Montepulciano Circle 36km/22mi
Today the route takes you through acres of vineyards as you make your way to Montepulciano. Views of Mount Amiata take your breath away as you ride into this famous wine town. Explore its streets and maybe taste a couple of wines before heading back, passing more vineyards and along the forest road, before cycling down back into Chianciano. You'll pass the Theia Spa on your way; perhaps use your free entrance at the end of the day.

Day 7: Pienza and Bagno Vignoni 35km/22mi
After a short transfer to Pienza take time to explore the town - it is one of the cheese capitals of Italy - and is beautiful mediaeval historic centre. Perhaps pick up a sandwich filled with Porchetta or a slab of rich and creamy Pecorino. The ride takes you downhill to cross one of the stunning plains of the Val dOrcia, and a short detour takes you to Roman Bagno Vignoni with its roman baths and sulphur springs. Follow a long straight Roman road then cross the valley and climb up and down into Chianciano.

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 before heading home.

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.


tour details

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