A Taste of Tuscany Self-Guided Cycling

A Taste of Tuscany Self-Guided Cycling

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Trip Fee

$ 2.180

Single Room Difference

$ 419

Date

25 July - 01 August 2026

Trip Information

Activity Areas

Cycling
E-Bike
Foodie Holidays
Self-Guided Cycling

Region & Country & City

Europe: Italy, Tuscany

Included in the Price

7 nights in 3-star equivalent accommodation
- All breakfasts and 4-course evening meals, plus one wine, olive oil and local produce tasting
- 1 thermal spa entrance
- Bike hire included, plus bike fitting and briefing at the start of your holiday
- Headwater navigation app

Not Included In The Price

Request a single room or e-bike if required, purchase travel insurance and arrange any visas and vaccinations. A compulsory solo traveller supplement applies to this holiday. Please be aware that the price excludes estimated local taxes/fees of 7 EUR.

Map

Itinerary

Day 1 Arrive in Chianciano Terme

Arrive at the Agriturismo La Pietriccia and enjoy a stroll to the old town, before your evening briefing by the owner, Stefano, and the first of many home cooked dinners.

Day 2 The Lakes Circuit

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

You will be transferred to Radicofani, the highest point in the Val d'Orcia, 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. Then make your way back to the agristurismo to enjoy the rest of your day.

Day 4 Sarteano Loop

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

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

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.

Travel Dates

25 July - 01 August 2026 $ 2.180

01 - 08 August 2026 $ 2.180

08 - 15 August 2026 $ 2.180

15 - 22 August 2026 $ 2.180

22 - 29 August 2026 $ 2.180

29 August - 05 September 2026 $ 2.180

05 - 12 September 2026 $ 2.390

12 - 19 September 2026 $ 2.390

18 - 25 September 2026 $ 2.390

19 - 26 September 2026 $ 2.390

26 September - 03 October 2026 $ 2.390

03 - 10 October 2026 $ 2.390

10 - 17 October 2026 $ 2.390

17 - 24 October 2026 $ 2.390

27 March - 03 April 2027 $ 2.180

03 - 10 April 2027 $ 2.180

10 - 17 April 2027 $ 2.180

17 - 24 April 2027 $ 2.180

24 April - 01 May 2027 $ 2.180

01 - 08 May 2027 $ 2.390

08 - 15 May 2027 $ 2.390

15 - 22 May 2027 $ 2.390

22 - 29 May 2027 $ 2.390

29 May - 05 June 2027 $ 2.390

05 - 12 June 2027 $ 2.390

12 - 19 June 2027 $ 2.390

19 - 26 June 2027 $ 2.390

26 June - 03 July 2027 $ 2.390

03 - 10 July 2027 $ 2.180

10 - 17 July 2027 $ 2.180

17 - 24 July 2027 $ 2.180

24 - 31 July 2027 $ 2.180

31 July - 07 August 2027 $ 2.180

07 - 14 August 2027 $ 2.180

14 - 21 August 2027 $ 2.180

21 - 28 August 2027 $ 2.180

28 August - 04 September 2027 $ 2.180

04 - 11 September 2027 $ 2.390

11 - 18 September 2027 $ 2.390

18 - 25 September 2027 $ 2.390

25 September - 02 October 2027 $ 2.390

02 - 09 October 2027 $ 2.390

09 - 16 October 2027 $ 2.390

16 - 23 October 2027 $ 2.390

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