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A Taste of Tuscany Cycling

A Taste of Tuscany Cycling

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  • Holiday typeSelf-guided cycling
  • Duration7 nights
  • Accommodationsingle-centre
  • Activity level
  • From $2085per person, tour only
  • Departures
    Every Saturday from 20 Apr '19 to 26 Oct '19
  • What your holiday price includes
  • 7 nights single-centre accommodation in a hotel
  • All buffet breakfasts and 4-course evening meals
  • Management by local hotelier
  • GPS route directions and maps
  • RideWithGPS navigation app
  • High quality bikes
  • Standard transfers to/from your hotel
  • Wine and olive oil tasting
  • One spa entrance
  • Cookery class
  • Optional Upgrades
  • Electric bikes available
  • City break add-ons in Rome
  • Excellent choice for
  • Food lovers, wine lovers, flora & fauna, bird spotting opportunities, art & history, swimming opportunities, vegetarian meals, couples, lake & river routes
      from 3 reviews

Mrs Sergeant says...
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 ...
Read reviews »


A Taste of Tuscany Cycling

  • Fabulous insight into traditional Tuscan life: the food, the wine, the culture
  • Exhilarating cycling across the UNESCO Val d'Orcia
  • Delicious classic Tuscan cuisine and cookery class
  • Visit the wine and cheese towns of Montepulciano and Pienza
  • Warm and welcoming agriturismo with a passionate owner

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, from a cookery class to hot spa baths and the chance to taste local wines and olive oils. Sample the Vino di Nobile of Monepulciano, rich Pecorino cheese in Pienza or take a bath in Roman Bagno Vignoni.

The cycling criss-crosses the UNESCO World Heritage Val d'Orcia and the rich fertile Valdichiana. You'll pass nature reserves, glistening lakes, the fortress of Radicofani, sitting dominantly on a rock on the highest point in the region and cycle through medieval towns, all on quiet roads or countryside gravel tracks.

Your base for the week is the modest but comfortable Agriturismo La Pietriccia, which stands on a hill with great views of Chianciano Vecchia. Stefano who runs the agriturismo will welcome you with his enthusiasm for everything to do with nature in the surrounding area. He will also lead the cookery course for you during your stay, and teach you all about the artisan products in the local area. The hotel produces 65% of what it serves on your table, and is surrounded by its own farm and orchards. There is a lovely terrace and swimming pool and lovely shady grassy area that looks out across the valley, where in the heat of summer you can take your dinner outside.

Mountain bikes are included on this holiday due to the terrain of 50% gravel.

If you wish to do both cycling and walking please call for details.

We're here to help

If you have any questions about this holiday call our sales team on 1-800-267-3347, use our live webchat or email usa@exodustravels.com

Day-by-day itinerary

We're here to help

If you've any questions about this holiday call our sales team on 1-800-267-3347 , or email usa@exodustravels.com

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. (Staying at the Agriturismo La Pietriccia for 7 nights, Half Board)

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 café 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 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

We take you back to the train station where you could possibly head to Florence or Rome for extra nights before heading home.

Where you stay

During your holiday you stay at the following hotels. If you'd like to extend your time at any of these or, if you'd like to enhance your stay with an upgraded room, just let us know at the time of booking.

To find out more call our sales team on 1-800-267-3347, use our live webchat or email usa@exodustravels.com

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Agriturismo la Pietriccia, Chianciano Terme

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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.

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.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Astoria Garden, Rome

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The 3-star Hotel Astoria Garden has a most unusual feature: an internal garden complete with banana and orange trees! Centrally located near the main railway station, but in a quiet residential street, this is a really good base from which to explore. There are 34 rooms, all air-conditioned and recently refurbished. They have telephone, television, and ensuite bathrooms.


Transfers included from Chiusi train station at 14:49, and back to Chiusi train station at 10:15.

Please call our sales team on 1-800-267-3347 or email usa@exodustravels.com to arrange connecting flights.


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.

Mrs Sergeant, 03/10/2018

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, 26/09/2018

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, 12/09/2018

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. Find out about The Headwater Price Promise to ensure you're getting the very best value for money.

For further details, or to check availability, speak to our sales team on 1-800-267-3347 or complete our holiday enquiry form (we'll contact you at a time that's most convenient for you).

To enquire about this holiday, or for further information, call our sales team on 1-800-267-3347 or complete our holiday enquiry form.

  • Apr
  • May
  • Jun
  • Jul
  • Aug
  • Sep
  • Oct
Apr 2019 Tour only Availability
20th Apr US$2085 Check availability
27th Apr US$2085 Check availability
May 2019 Tour only Availability
4th May US$2085 Check availability
11th May US$2195 Check availability
18th May US$2195 Check availability
25th May US$2195 Check availability
Jun 2019 Tour only Availability
1st Jun US$2195 Check availability
8th Jun US$2195 Check availability
15th Jun US$2195 Check availability
22nd Jun US$2195 Check availability
29th Jun US$2225 Check availability
Jul 2019 Tour only Availability
6th Jul US$2225 Check availability
13th Jul US$2225 Check availability
20th Jul US$2225 Check availability
27th Jul US$2225 Check availability
Aug 2019 Tour only Availability
3rd Aug US$2225 Check availability
10th Aug US$2225 Check availability
17th Aug US$2225 Check availability
24th Aug US$2225 Check availability
31st Aug US$2255 Check availability
Sep 2019 Tour only Availability
7th Sep US$2255 Check availability
14th Sep US$2255 Check availability
21st Sep US$2255 Check availability
28th Sep US$2255 Check availability
Oct 2019 Tour only Availability
5th Oct US$2255 Check availability
12th Oct US$2255 Check availability
19th Oct US$2255 Check availability
26th Oct US$2255 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

This holiday is unsuitable for children.

Holiday type
Self-guided cycling Managed locally by hotelier.

Every Saturday from 20th Apr 2019 to 26th Oct 2019, for 7 nights.

All buffet 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. Please call us for further details.

Tailor-made travel

Tour only
Transfers included from Chiusi train station at 14:49, and back to Chiusi train station at 10:15.

How to book

For further details, or to check availability, speak to our sales team on 1-800-267-3347 or complete our holiday enquiry form (we'll contact you at a time that's most convenient for you).

To enquire about this holiday, or for further information, call our sales team on 1-800-267-3347 or complete our holiday enquiry form.

We are ATOL registered We are an ABTA member
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