Skip to main content

Italy: Tuscany

A Taste of Tuscany Cycling

Trip code: C07ST

Average customer rating 4.9 / 5(33 verified reviews)

Self-Guided Cycling
7 nights single centre
Moderate
CO₂ rating 1/5
Headwater Navigation app

Trip highlights

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

Item 1 of 1

Trip details

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.

What's included

Included

  • 7 nights in 3-star equivalent accommodation
  • All breakfasts and all evening meals
  • Bike fitting and briefing at the start of your holiday
  • Headwater navigation app
  • Bike hire included
  • 1 thermal spa entrance

Not included

  • Flights
  • Local taxes/fees
  • Travel insurance

Your bike

Hand-picked for the route, hire included

Haibike, Seet Hardseven 3.0 or equivalent. Your bike hire is included in the price of your holiday and comes equipped with the relevant essentials, plus phone holder.

Haibike Seet Hardseven 3.0

Travel options

Our travel specialists can arrange flights, rail and transfers to this holiday from wherever you are. Call us to plan your journey. +44 1606 720099

Itinerary

Route map, with each night's stop marked
The full route, night by night. Select the map to view it full screen.

Day 1 · —Arrive in Chianciano Terme

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

Pool and view at La Pietriccia
equivalent

Agriturismo la Pietriccia

Chianciano Terme

  • Air conditioning
  • Diners Club
  • Hairdryers
  • Mastercard
  • Other email access
  • Safe
  • Swimming pool
  • Tea & coffee
  • Television
  • Visa cards

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 · 41km/25.5miThe Lakes Circuit

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.

Elevation

The Lakes Circuit elevation profile

Day 3 · 34km/21.1miRadicofani

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.

Elevation

Radicofani elevation profile

Day 4 · 39km/24.2miSarteano Loop

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.

Elevation

Sarteano Loop elevation profile

Day 5 · —Free day

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 · 36km/22.4miMontepulciano Circle

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.

Elevation

Montepulciano Circle elevation profile

Day 7 · 35km/21.7miPienza and Bagno Vignoni

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.

Elevation

Pienza and Bagno Vignoni elevation profile

Day 8 · —Leave Chianciano Terme

Leave Chianciano Terme

Leave Chianciano Terme.

Extending your holiday

Exterior of the Hotel Canada Roma

Hotel Canada Roma

Rome

  • Air conditioning
  • American Express
  • ATM
  • Bank
  • Hairdryers
  • Market
  • Mastercard
  • Safe
  • Shops
  • Tea & coffee

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.

What our travellers say

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

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

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

Excellent organisation. Extremely enjoyable. Highly recommended!

Mr Garraway

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

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

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

Mrs Michael

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

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

Mr Suddes

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

Mr Polge
Item 1 of 1

Positive impact

Carbon score for this trip

14.0

Kg CO₂e

per person, per night

Relative to other Headwater trips

We measure emissions from the parts of the holiday we organise — including accommodation, in-trip transport, meals and activities — and express them as CO₂e per person, per night. Our label doesn’t include your travel to and from the start of the trip. As a Certified B Corp, Headwater is committed to reducing this figure and to positively impacting local communities, the local environment and our staff. Learn more

From£1,349per person