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A Taste of Tuscany Cycling

0044 1606 720199

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  • Holiday code
    C07ST
  • Holiday type
    Self-guided cycling
  • Duration
    7 nights
  • Accommodation
    single-centre
  • Activity level
  • From $2750per person, tour only
  • Departure months
    JFMAMJJASOND
  • What your holiday price includes
  • 7 nights single-centre accommodation in a hotel
  • All breakfasts and 4-course evening meals
  • Bike fitting and briefing at the start of your holiday
  • Headwater navigation app
  • Bike hire included
  • Standard transfers to/from your hotel (if booking inclusive flights)
  • Wine, olive oil and local produce tasting
  • 1 thermal spa entrance
  • Optional Upgrades
  • Electric bikes available
  • City break add-ons in Rome
  • City-break add-on in Rome
  • Single occupancy
  • Travel options and Transfers
  • Suitable for
  • Couples
  • Excellent choice for
  • Food lovers, wine lovers, flora & fauna, bird spotting opportunities, art & history, swimming opportunities, vegetarian meals, lake & river routes
      from 22 reviews

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, ...
Read reviews »

Italy: Tuscany

A Taste of Tuscany Cycling

  • Fabulous local insight into traditional Tuscan life: the food, the wine, the culture
  • Exhilarating cycling across the UNESCO Val d'Orcia
  • Delicious classic, home cooked Tuscan cuisine - with 'km 0' cooking (all local food)
  • Visit the wine and cheese towns of Montepulciano and Pienza
  • Warm and welcoming agriturismo (farmhouse accommodation) with a passionate owner - the best of Italian hospitality

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.



We're here to help

If you have any questions about this holiday call our sales team on 0044 1606 720199, use our live webchat or email sales@headwater.com

Cycling information

Distances vary, parts of the countryside are fairly hilly, so you can take your time on the steeper climbs and admire the wonderful long-distance views.




We're here to help

If you've any questions about this holiday call our sales team on 0044 1606 720199 , or email sales@headwater.com

Day 1: Arrive in Chianciano Terme

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

Day 2: The Lakes Circuit 41km/26mi

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

Day 3: Radicofani 34km/21mi

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

Day 4: Sarteano Loop 39km/24mi

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

Day 5: Free day

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

Day 6: Montepulciano Circle 36km/22mi

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

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 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

Day 8: Leave Chianciano Terme

Leave Chianciano Terme.
Breakfast included

Where you stay

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.

Agriturismo la Pietriccia, Chianciano Terme

Swimming Pool IconHair dryer icon NEARBY:

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 agriturismo's apartments, these are located 100m from the main agriturismo.

Extending your stay

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.

Hotel Canada Roma, Rome

Hair dryer icon

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.


Room upgrades: Deluxe and junior suite
Deluxe rooms are larger with a more stately decor.
Junior suites have a separate living room.

Travel

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.

Reviews

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.


Clare Nicholson, 23/09/2023

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.


Veronica Hudson, 15/09/2023

‘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.


Elizabeth Leitch, 26/08/2023


TRIVEDI, 10/06/2023

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.


NEALE, 10/06/2023

Excellent, although some of the cycling was tougher than expected. Would get an Ebike next time!


PETCH, 03/06/2023

We had an excellent overall experience


JONES, 13/05/2023

Overall our holiday was excellent, aided very much by the attention of our host Stefano Mazzetti


Mr Ross, 17/09/2022

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.


Mr Wermann, 03/09/2022

We have travelled with Headwater pre and post dependent children for over 25 years and loved every trip. Locations and itineraries alwasys spot on.


Mr Vaesen, 04/06/2022

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.


Dr Myatt, 16/04/2022

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.


Mr Perryer, 19/09/2020

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


Mr Polge, 21/09/2019

Headwater holidays definitely seem to include the eating experience as very important. They are well put together and well located.


Mr Suddes, 14/09/2019

Excellent centre for exploring rural Tuscany that was off the usual tourist trail.


Ms Dean, 07/09/2019

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


Mrs Michael, 31/08/2019

Great holiday if you like mountain bikes and fairly rough terrain. Beautiful countryside and friendly people, wonderful Agriturismo accommodation.


Mr Baston, 31/08/2019

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.


Mr Powell, 31/08/2019

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.


Mr Garraway, 22/06/2019

Excellent organisation. Extremely enjoyable. Highly recommended!


Mrs Sergeant, 22/09/2018

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.


Mrs Stanley, 08/09/2018



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.


Mrs Kenn, 18/08/2018

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.



Dates and prices

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

Bike fitting and briefing at the start of your holiday

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.

  • Apr 2024
  • May 2024
  • Jun 2024
  • Jul 2024
  • Aug 2024
  • Sep 2024
  • Oct 2024
DepartingTour only Prices   Single supplement
6th Apr 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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13th Apr 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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18th Apr 2024 US$2790 US$441 Tour only: US$2790
Single supp: US$441
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20th Apr 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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27th Apr 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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DepartingTour only Prices   Single supplement
4th May 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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11th May 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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18th May 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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25th May 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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DepartingTour only Prices   Single supplement
1st Jun 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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8th Jun 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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15th Jun 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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22nd Jun 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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29th Jun 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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DepartingTour only Prices   Single supplement
6th Jul 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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Check availability
13th Jul 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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20th Jul 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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27th Jul 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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DepartingTour only Prices   Single supplement
3rd Aug 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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Check availability
10th Aug 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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17th Aug 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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24th Aug 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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31st Aug 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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DepartingTour only Prices   Single supplement
7th Sep 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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14th Sep 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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21st Sep 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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28th Sep 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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DepartingTour only Prices   Single supplement
5th Oct 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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Check availability
12th Oct 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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19th Oct 2024 US$2750 US$441 Tour only: US$2750
Single supp: US$441
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Check availability

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.

Holiday details

Solo travellers
Please call for details and prices

Children
This holiday is unsuitable for children.

Holiday type
Self-guided cycling Managed by Headwater rep.

Departures
Every Saturday from 6th Apr 2024 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.

Tailor-made travel

Tour only

How to book

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.