Clare Nicholson says...
We are not regular cyclists so self guiding using the app allowed us to go at our own pace but with backup from the local host. The app was easy to use, ...
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This is not just a cycling holiday it is an immersion into local Tuscan life, from hot thermal spa baths to the chance to taste local wines and olive oils. Sample the Vino Nobile of Montepulciano, rich Pecorino cheese in Pienza or take a bath in Roman Bagno Vignoni.
Please note that due to the terrain of 50% gravel, mountain bikes are provided on this holiday.
See more of this trip on our Youtube channel - click here watch.
Arrive at the family run Agriturismo La Pietriccia. Enjoy a stroll in the old town before your evening briefing and the first of many home cooked dinners.
Evening meal included
Start the week with mountain views and forest tracks as you head to the small town of Montallese and on to Lake Chiusi. After a lunch-break take the long distance path of Sentiero della Bonifica to the Lake of Montepulciano, a nature reserve ideal for bird-watching, before heading back to the agristurismo in time for dinner.
Breakfast and evening meal included
You will be transferred to Radicofani, the highest point in the Val d'Orca, for incredible views. From here cycle to Contignano, famous for its pecorino cheese and a perfect spot for lunch before a downhill stretch through the forest and past the beautiful private gardens of La Foce. The back to the agristurismo in time for wine and local produce tasting in the old town before dinner.
Breakfast and evening meal included
Descend along country tracks passing a truffle-growing area before crossing the Astrone stream. Cycle through beautiful valleys to the medieval town of Sarteano before carrying on to Cetona, then climb to Mondo X where you can find one of the best restaurants in Italy, La Frateria - a beautiful convent started by St Francis in 1212. Head back to your hotel in time for your dinner.
Breakfast and evening meal included
Spend the day relaxing, enjoy an olive oil tasting at the agriturismo or walk into Chianciano Vecchia to see the Etruscan Museum of Chianciano Terme. On your way back to the hotel you could use your thermal spa voucher and relax in the healing waters.
Breakfast and evening meal included
Cycle through acres of vineyards on your way to Montepulciano and stop to take in views of the famous Mount Amiata. Explore Montepulciano's winding medieval streets before cycling back to Chianciano.
Breakfast and evening meal included
After a short transfer to Pienza take time to explore the town - it is one of the cheese capitals of Italy - and its beautiful medieval 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 d'Orcia, 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.
Breakfast and evening meal included
Leave Chianciano Terme.
Breakfast included
This single-centre holiday is based at the following hotel. If you'd like to extend your stay here, or upgrade your room, just let us know at the time of booking.
To find out more call our sales team on 0044 1606 720199 or email sales@headwater.com
Find out more on the hotel website.
Read customer reviews on Tripadvisor.
NEARBY:
If you'd like to extend your trip with extra nights at the start or end, or if you'd like to arrange a stop off point en-route, then we recommend the following hotels.
Read customer reviews on Tripadvisor.
Room upgrades: Deluxe and junior suite
Deluxe rooms are larger with a more stately decor.
Junior suites have a separate living room.
Transfers can be arranged at a supplement from Chiusi train station at 14:49, and back to Chiusi train station at 10:15.
Call now to speak to our specialist team at 0044 1606 720199 or email us at sales@headwater.com for enquiries or to book your trip.
Everyone who goes on a Headwater holiday will be emailed a link to our post-holiday questionnaire where they can give us an honest assessment of all aspects of their holiday - everything from how quickly we answer the phone to how clean the hotels were - plus an overall rating and comments about their holiday.
Any feedback collected is posted to our website, so that people can make an informed decision based on past experiences before heading off on holiday. We don’t edit the reviews, the only thing we do is proofread them and alter any typos, where necessary, to ensure they are easy to read for everyone. All reviews will be published (except in certain extreme circumstances), and a member of the Headwater team will respond to any constructive criticisms/comments under the reviews, at their discretion. So, for the real tales, twists and turns of our holidays, look no further than the reviews from our previous travellers.
We are not regular cyclists so self guiding using the app allowed us to go at our own pace but with backup from the local host. The app was easy to use, the routes were excellent, and the hotel a lovely place to relax at the end of the day.
‘For our first e-bike holiday we were challenged by the first route and length of ride( 41km) and would prefer the option of more rest days - perhaps have Day 3 as rest day. There was no information for activities/ sightseeing information on rest days and we were fortunate that our host Stefano was amenable and very knowledgeable of the area and assisted us in transport and background information of the areas to visit.
Overall an excellent holiday. The hotel was in a beautiful location with easy access to facilities in the town. Good routes and great e-bikes which were essential for this region in our opinion. The hotel staff were very friendly and quintessentially italian ! They did all they could to accommodate one of our party who does not eat meat.
Excellent, although some of the cycling was tougher than expected. Would get an Ebike next time!
We had an excellent overall experience
Overall our holiday was excellent, aided very much by the attention of our host Stefano Mazzetti
Wonderful welcome and support from Stefano and his team. Beautiful rides with some amazing views through varied terrain in the Val d'Orcia, challenging at times but not too much to handle. Lovely pool, ideal for a wind down after a day in the saddle. We looked forward to dinner every night, cooked with love from local produce. Excellent value home produced wines. We highly recommend this holiday. The Headwater team were incredibly helpful and efficient in answering our queries and arranging transfers. It is so refreshing (and so rare nowadays) to be able to speak to named helpful people who know what they are talking about.
We have travelled with Headwater pre and post dependent children for over 25 years and loved every trip. Locations and itineraries alwasys spot on.
Good cycle routes through lovely countryside. Accommodation in Rome was excellent, with very attentive staff. Accommodation at Agriturismo La Peitriccia was disappointing, but Stefano was very helpful.
For me this was to an excellent cycling holiday in the heart of the Tuscan Val d’Orcia, considering I was an ‘senior’ solo rider in early season. The hire of an E-MTB bike was a boon for the hilly ’strade bianche’ (gravel roads). A week at the Agriturismo ‘La Pietriccia’ was a very good choice. Stefano, the main host and his brother Simone, were extremely helpful in everything. From organising me on and off the suggested App routes, to giving me a beer when I got back and providing tasty 4 course meals in the evening. The ‘tasting’ at BradiToscani food/wine shop and the Chianciano Thermal Spa arranged visits were a delight. The cookery session was unfortunately cancelled because of Covid restrictions but was substituted with an enjoyable local pizzeria visit.
Highly recommended to any cycling Italophiles.
We had an amazing week with Stefano and his family and team. The equipment was excellent and the cycling amazing, pretty challenging, but we got to see the beautiful countryside and villages of the region. The food at La Pietriccia was outstanding. Despite the Covid restrictions Stefano did everything he could to help us keep our plans flexible so that we could complete all the routes. We would certainly recommend this holiday for people like us, who like their cycling, wine and food in equal measures.
Headwater response:
Thank you so much for sharing your experience. We are all delighted that you had an amazing holiday and we hope we can welcome you on another trip with us again soon.
Headwater Customer Services Team
Headwater holidays definitely seem to include the eating experience as very important. They are well put together and well located.
Excellent centre for exploring rural Tuscany that was off the usual tourist trail.
Great trip, cycling is relatively challenging due to steep Tuscany hills and gravel roads but the scenery more than makes up for it! The food and welcome is fantastic, if you have the opportunity do the cookery course. Stefano is both educational and passionate.
Thoroughly enjoyed my stay
Great holiday if you like mountain bikes and fairly rough terrain. Beautiful countryside and friendly people, wonderful Agriturismo accommodation.
The location is perfect for quiet (often off road) cycling. Roads and gravel tracks gave access to a variety of stunning scenery. There was plenty of opportunity to experience the culture, local food and drink.
Our base for the week, Agriturismo ‘La Pietriccia’, a small family-run farm, was idyllic and the hosts very friendly, welcoming and entertaining!
Excellent mountains bikes were provided and were ideal for the hilly, gravelly terrain. We greatly enjoyed pedal cycling but the option of e-bikes would be a very good alternative for those less confident or fit. The routes gave a splendid variety and were never repetitive. It was a fabulous week.
A great taste of Tuscany - scenery, food and wine were all lovely! Stefano was very helpful, ensuring that the holiday would cater for each individual's needs. The fact that about 50% of the recommended routes were on gravel tracks (varying from flat, easy to ride sections, to quite steep and slightly more challenging sections) made the provision of mountain bikes most welcome.
Excellent organisation. Extremely enjoyable. Highly recommended!
This was a wonderful holiday in all respects. We loved the family atmosphere at La Pietriccia, everyone was very friendly and helpful and the food was delicious. Stefano is passionate about the food he serves and was very happy to share his knowledge and expertise. He also helped us to amend the cycling routes to avoid some of the more difficult terrain, which was greatly appreciated. We expected hills but steep gravel tracks were challenging until we swapped to electric bikes for the last two days and it was a completely different experience. We would wholeheartedly recommend this holiday.
We had a wonderful holiday. Tuscany is beautiful and La Pietriccia a little gem. Stefano (the owner) runs a highly efficient setup with his helpful and friendly staff. He is one of those rare men who can multi-task (!) whether it’s reorganizing our cycle routes, finding new routes for others, briefing groups, getting bicycles mended, cooking and so on and all with a smile and quick wit. We were impressed that groups were given GPS locators in case they got lost and so clearly a lot of thought had gone into making the best experience for guests. I would thoroughly recommend this holiday.
This was a really good holiday, the cycling was challenging in the heat so we would recommend early morning starts or later in the day cycling! Stefano the agritourismo owner could not have been more helpful and informative, the hotel was charming and all the staff very good and helpful. The food was really excellent and we would definitely recommend taking up the option of the wine and food event in the local town. Have already recommended this holiday to friends.
You can be confident that our pricing includes all the standard requirements of your holiday and many additional extras. Always ensure that you are comparing like for like when booking your holiday.
This 7 night self-guided cycling holiday includes:
Single-centre accommodation in a hotel
All breakfasts and 4-course evening meals
Management by local hotelier
Headwater navigation app for your smartphone
Bike hire
Standard transfers to/from your hotel (if booking inclusive flights)
Wine, olive oil and local produce tasting
1 thermal spa entrance
How to book:
To book this holidays speak to our sales team on 0044 1606 720199 or click on the appropriate 'book now' or 'check availability' button below.
To book this holiday call our sales team on 0044 1606 720199 or click on the appropriate 'Book now' or 'check availability' button below.
Departing | Tour only | Prices ![]() |
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7th Oct 2023 | US$2499 | US$412 | Tour only: US$2499 Single supp: US$412 |
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14th Oct 2023 | US$2499 | US$412 | Tour only: US$2499 Single supp: US$412 |
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21st Oct 2023 | US$2499 | US$412 | Tour only: US$2499 Single supp: US$412 |
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6th Apr 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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13th Apr 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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20th Apr 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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27th Apr 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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Departing | Tour only | Prices ![]() |
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4th May 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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11th May 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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18th May 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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25th May 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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Departing | Tour only | Prices ![]() |
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1st Jun 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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8th Jun 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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15th Jun 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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22nd Jun 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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29th Jun 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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Departing | Tour only | Prices ![]() |
Single supplement | |
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6th Jul 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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13th Jul 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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20th Jul 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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27th Jul 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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Departing | Tour only | Prices ![]() |
Single supplement | |
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3rd Aug 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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10th Aug 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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17th Aug 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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24th Aug 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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31st Aug 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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Departing | Tour only | Prices ![]() |
Single supplement | |
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7th Sep 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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14th Sep 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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21st Sep 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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28th Sep 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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Departing | Tour only | Prices ![]() |
Single supplement | |
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5th Oct 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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12th Oct 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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19th Oct 2024 | US$2679 | US$412 | Tour only: US$2679 Single supp: US$412 |
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The prices quoted for each individual departure supercede those published in our current brochures. Air prices are subject to change and we advise early booking to obtain the best prices. Please see our Planning your holiday and What's included in the price? pages for additional information.
Solo travellers
Please call for details and prices
Children
This holiday is unsuitable for children.
Holiday type
Self-guided cycling Managed locally by hotelier.
Departures
Every Saturday from 7th Oct 2023 to 19th Oct 2024, for 7 nights. All dates are subject to availability, please contact us to check.
Meals
All breakfasts and 4-course evening meals
Electric bikes
It is possible to hire electric bikes for this holiday at a supplement of £110 per person. As these are available on a first come first served basis, we recommend early booking to avoid disappointment.
Tour only
Transfers can be arranged at a supplement from Chiusi train station at 14:49, and back to Chiusi train station at 10:15.
To book this holidays speak to our sales team on 0044 1606 720199 or click on the appropriate 'book now' button above.
If you need further information before you book simply complete our Holiday Enquiry Form and a member of our sales team will get back to you.
To book this holiday call our sales team on 0044 1606 720199 or click on the appropriate 'Book now' or 'Check availability' button below.