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A Taste of Tuscany Self-Guided Cycling
Find trips›Italy›A Taste of Tuscany Self-Guided Cycling
EXOperated by Exodus Adventure Travels

A Taste of Tuscany Self-Guided Cycling

From
CAD 2,710
Duration
8 days
Countries
Italy
Activity
easy

The adventure

This single-centre self-guided 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 wine and oil sampling to hot thermal spa baths and the

At a glance

Duration
8 days
Route
→
Countries
Italy
Activity level
easy
Style
Cycling, Food & Drink, Wellness & Yoga
Group size
Ask
Flights
Not included
Solo travellers
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Day by day

View of a historic hilltop town surrounded by lush greenery under cloudy skies.
Your journey through

Italy

Showing Days 1-7

8-day itinerary

Day 1Arrive in Chianciano TermeArrive 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.
Narrow cobblestone street amidst lush green trees leading to stone arch against sunset sky in old town of Chianciano TermeChianciano 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.
Map showing Chianciano Terme
Day 2The Lakes CircuitStart 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.
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 3RadicofaniYou 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.
Explore the picturesque alleys of Ostuni, Apulia, with sunlit whitewashed buildings and green shutters.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.
Map showing Radicofani
Day 4Sarteano LoopDescend 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.
Aerial top view of empty curvy asphalt road running through rough heath in daylightSarteano 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.
Map showing Sarteano Loop
Day 5Free DaySpend 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.
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 6Montepulciano CircleCycle 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.
Explore the historic and charming streets of Montepulciano, Tuscany, with its iconic clock tower and old town vibe.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.
Map showing Montepulciano Circle
Day 7Pienza and Bagno VignoniAfter 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.
A panoramic view of the historic town of Pienza, Tuscany, with Renaissance architecture.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.
Map showing Pienza and Bagno Vignoni
1 / 2

What's included

Included
  • ✓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

Discover Italy

A glimpse of the destination you'll explore.

Picturesque landscape of Lake Garda with a distant island under a summer sky.
Overcast day in Tuscan hills featuring cypress trees and traditional stone house.
A picturesque town nestled by cliffs on the Amalfi Coast, Italy.
Picturesque view of Tuscany's rolling hills, vineyards, and Italian villas under a clear summer sky.
Beautiful view of Ponte Sant'Angelo spanning the Tiber River in Rome, Italy under a clear sky.

Upcoming departures

DatesPrice / personAvailability
8 Aug – 15 Aug 2026
CAD 2,710On request
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15 Aug – 22 Aug 2026
CAD 2,710On request
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22 Aug – 29 Aug 2026
CAD 2,710On request
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29 Aug – 5 Sep 2026
CAD 2,710On request
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EX
Operated by Exodus Adventure Travels

TripFinder compares the available catalog facts and Brandi Leanna can handle the booking — and you pay the same as booking Exodus Adventure Travels direct, never more, because the operator pays our commission. You travel under the operator's terms; final price and availability are confirmed before purchase.

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From
CAD 2,710 CAD / person
Twin share · prices may vary by departure
Next departures
Aug 8, 2026CAD 2,710 · on request
Aug 15, 2026CAD 2,710 · on request
Aug 22, 2026CAD 2,710 · on request
See all 42 departures →
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✓Booked through Trevello Travel Group, TICO Reg. #5003057 — handled under Ontario travel law.
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