Italy : Tuscany

A Taste of Tuscany Cycling

Trip code: C07ST 4.9 (24 reviews)

Self-guided cycling

7 nights,
single centre

Level: 2+
Moderate plus

14.0Kg CO2e

Navigation App

e-bike hire


  • 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


  • 7 nights accommodation
  • All breakfasts and 4-course evening meals
  • Bike fitting and briefing at the start of your holiday
  • Headwater navigation app
  • Bike hire included
  • Wine, olive oil and local produce tasting
  • 1 thermal spa entrance


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.


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.

See more of this trip on our Youtube channel - click here watch.




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.

You stay at Agriturismo la Pietriccia.

hotel details

 equivalent

Agriturismo la Pietriccia, Chianciano Terme



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.

Day 2: The Lakes Circuit (41km/25.5mi)

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.


Day 3: Radicofani (34km/21.1mi)

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.


Day 4: Sarteano Loop (39km/24.2mi)

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.


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.

Day 6: Montepulciano Circle (36km/22.4mi)

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.


Day 7: Pienza and Bagno Vignoni (35km/21.7mi)

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.


Day 8: Leave Chianciano Terme

Leave Chianciano Terme.

Extending your holiday

If you'd like to extend your trip with extra hotel nights we recommend: Hotel Canada Roma, Rome.

hotel details


Hotel Canada Roma, Rome


Cash machine

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.



These tour only prices are based on two people sharing. Single supplement from $441.

These flight inclusive prices are based on two people sharing. Single supplement from $441.

  • Alternative flights, including regional departures
  • Electric bikes
  • City-break add-on in Rome
  • Single occupancy
  • Travel options and Transfers

Call now to speak to our specialist team at 0044 1606 720199 or email us at for enquiries or to book your trip.


Our second Headwater cycling holiday - we definitely needed e-bikes as well as mountain bikes as some tricky terrain and steed gradients. We had a great time but there were moments which were challenging.

Rosemary Dean, 4 May 2024


Excellent from first to last contact. The decision to upgrade to e bikes was not regretted. There are a lot of uphill in the routes and we managed these with ease and comfort, even at the end of a long day. The charge was easily sufficient and even after a hard day's cycling had loads of charge and range left. The bikes were heavy beasts though! The Headwater app, route notes and voice commands were very good.....a couple of times the voice command contradicted the route on the app but wasn't a big issue as we re-routed quickly. Stephano was a wonderful host. The specially prepared vegan meals for my partner were superb and generous ( as we're all the meals at La Pietriccia ). Our room was super comfortable and the cycle trips fantastic. I gave Stephano a 5* review independently only because l couldn't leave a 10* review!

Norman Crutchley, 6 Apr 2024


Very well organised

David Hrouda, 5 Apr 2024


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.

Clare Nicholson, 23 Sep 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.

Veronica Hudson, 15 Sep 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.

TRIVEDI, 10 Jun 2023


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

NEALE, 10 Jun 2023


We had an excellent overall experience

PETCH, 3 Jun 2023


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

JONES, 13 May 2023


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 Ross, 17 Sep 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 Wermann, 3 Sep 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.

Mr Vaesen, 4 Jun 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.

Dr Myatt, 16 Apr 2022


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.

Mr Perryer, 19 Sep 2020


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

Mr Polge, 21 Sep 2019


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

Mr Suddes, 14 Sep 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

Ms Dean, 7 Sep 2019


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

Mrs Michael, 31 Aug 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 Baston, 31 Aug 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 Powell, 31 Aug 2019


Excellent organisation. Extremely enjoyable. Highly recommended!

Mr Garraway, 22 Jun 2019


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 Sergeant, 22 Sep 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 Stanley, 8 Sep 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.

Mrs Kenn, 18 Aug 2018


Self-guided cycling

7 nights,
single centre

Level: 2+
Moderate plus

14.0Kg CO2e

Navigation App

e-bike hire

7 nights from $2750


Call: +44 1606 720199