TripFinder

Compare multi-day small-group tours from independent operators, then ask a Canadian travel advisor for help.

Explore

Find tripsDestinationsTravel stylesDealsCompare trips

TripFinder

How it worksTalk to an agentAbout usContact

Good to know

Privacy PolicyCookie choicesTerms of UseTravel guides
TripFinder.ca helps you compare small-group trips from independent operators and book with a TripFinder travel advisor. Trips are operated by the tour companies under their own terms. © 2026 HighBar Enterprises Ltd.Made for adventurers in Canada 🍁
TripFinder
Find trips
DealsAsk TheoCompareHow it worksBrowse all trips
A Taste of Tuscany Cycling
Find trips›Italy›A Taste of Tuscany Cycling
EXOperated by Exodus Adventure Travels

A Taste of Tuscany Cycling

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

The adventure

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 wine and oil sampling to hot thermal spa baths and the chance

At a glance

Duration
8 days
Route
→
Countries
Italy
Activity level
easy
Style
Cycling, Food & Drink, Multi-Country / Grand Tour, Wellness & Yoga
Group size
Ask
Flights
Not included
Solo travellers
Ask an agent

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. (Staying at the Agriturismo La Pietriccia for 7 nights, Half Board)
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. (Staying at the Agriturismo La Pietriccia for 7 nights, Half Board)
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'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 Agriturismo in time for wine and local produce tasting in the old town before dinner.
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'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 Agriturismo in time for wine and local produce tasting in the old town before dinner.
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

Where you'll stay & how you'll travel

Accommodation
  • Overview
  • Itinerary
  • Dates & Prices
  • Accommodation
  • Essential Info
  • Reviews
  • All buffet breakfasts and 4-course evening meals
  • Headwater Navigation App
  • High Quality Bikes
  • Wine, olive oil and local produce tasting
  • 1 thermal spa entrance
  • Fabulous local insight into traditional Tuscan life: the food, the wine, the culture
Meals
  • Overview
  • Itinerary
  • Dates & Prices
  • Accommodation
  • Essential Info
  • Reviews
  • All buffet breakfasts and 4-course evening meals
  • Headwater Navigation App
  • High Quality Bikes
  • Wine, olive oil and local produce tasting
  • 1 thermal spa entrance
  • Fabulous local insight into traditional Tuscan life: the food, the wine, the culture

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(price may vary)
CAD 2,710On request
Book my trip
15 Aug – 22 Aug 2026(price may vary)
CAD 2,710On request
Book my trip
22 Aug – 29 Aug 2026(price may vary)
CAD 2,710On request
Book my trip
29 Aug – 5 Sep 2026(price may vary)
CAD 2,710On request
Book my trip
EX
Operated by Exodus Adventure Travels

TripFinder compares the available catalog facts and can help with the booking. You travel under the operator's terms; final price and availability are confirmed before purchase.

Book my trip →
Ask Theo about this trip
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 →
Book my trip
No payment now — tell us a few details and an expert confirms everything & finishes your booking.
✓No payment & no obligation to send a request
✓An expert confirms by email or phone — your choice
Prefer to talk first? Send a request and choose phone as your contact preference.
Operated by Exodus Adventure Travels · view on operator site ↗

More Europe adventures

OpeningZagreb to Santorini: 35 Unforgettable Days image
GG Adventures
Save 20%

Zagreb to Santorini: 35 Unforgettable Days

Bosnia and Herzegovina, Albania, Greece, Montenegro, Croatia · 35 days · Easy

fromCAD 8,639
Next: 09 Aug
OpeningUltimate Europe: Berlin, Tuscany & Greek Temples image
GG Adventures
Save 35%

Ultimate Europe: Berlin, Tuscany & Greek Temples

Albania, Austria, Czechia, Greece, Netherlands, Montenegro, Germany, Italy, Croatia · 34 days · Easy

fromCAD 5,960
Next: 09 Aug
OpeningOne Month in Europe: Germany, Italy & Croatia image
GG Adventures
Save 25%

One Month in Europe: Germany, Italy & Croatia

Albania, Austria, Czechia, Greece, Netherlands, Montenegro, Germany, Italy, Croatia · 30 days · Easy

fromCAD 5,310
Next: 09 Aug
From
CAD 2,710/ person
Book my trip