Join us on two wheels in Tuscany and experience one of the true cycling classics! Cyclists can expect cypress-lined horizons, world-renowned historical treasures and the best Italian food in all the land when they embark on a cycling tour of Tuscany. This really is one of those must-visit destinations that is best explored by bike. You can enjoy this region by either one of our guided or self-guided tours, allowing you to enjoy Tuscany your way.
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Destinations (1)
Types of Cycling / Grades (1)
Departure Month
Level of Support
Destinations (1)
Types of Cycling / Grades (1)
Departure Month
Level of Support
Leisure Cycling in Tuscany
Road Cycling in Tuscany
Mountain Biking in Tuscany
Gravel Riding in Tuscany
Family Cycling in Italy
All Cycling Holidays in Italy
Cycling in Sardinia
Cycling in Puglia
Cycling in The Alps and Dolomites
Cycling in Prosecco Region
Cycling in Emilia-Romagna
Cycling in Sicily
Cycling in Lake Garda
Bike and Boat
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Guided
Coast to Coast - L'Adriatico al Tirreno
Guided Road Bike Tour
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SAVE ON 2026 ESCAPES
Save $125 on this holiday when you book before 10 November 2025. Enter promo code BN26 when you book and your discount will be applied after your booking is confirmed. Ts and Cs apply.
| Start Date | End Date | Price p.p. |
|---|---|---|
| * 16/05/2026 | 24/05/2026 | $3,850.00 |
| * 12/09/2026 | 20/09/2026 | $3,850.00 |
- An epic coast to coast journey riding all the way from the Adriatic coast to the Tyrrhenian Sea
- Cycling through the smallest republic in Europe, San Marino
- Easing along the rolling Nove Colli hills, the routes of the famous Italian Gran Fondo
- Visiting historical sites such as the Palazzo Ducale in Orvieto and San Francis Abbey in Assisi
- Staying in quality accommodation, with fantastically warm hospitality
- Riding to Gubbio and Assisi, UNESCO World Heritage sites
Self-Guided
Tuscany - Giro della Toscana
Self-Guided Road Bike Tour
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
2026 29 Mar – 26 Oct (excluding dates in July and August)
Season 1 – $2425 29 Mar – 14 Jun and 09 Sep – 26 Oct
Season 2 – $2895 15 Jun – 30 Jun and 01 – 08 Sep
To ensure you have the best experience possible, we’d recommend travelling in the Spring or in the Autumn. We don’t as standard offer this tour in the hotter, more humid, busier summer months of July and August. If however your dates are set in July or August, please call us for a chat and we’ll do what we can to accommodate you.
- Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting along the way
- Staying in quality accommodation, with fantastically warm hospitality
- Easing along the rolling hills of the ‘Colli Sienesi’
- Riding the stunning UNESCO heritage region of Val d’Orcia
- Stopping off at the lovely San Gimignano and Montalcino
- Chilling out with a post-ride Chianti
Guided
Tuscany - Giro della Toscana
Guided Road Bike Tour
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SAVE ON 2026 ESCAPES
Save $125 on this holiday when you book before 10 November 2025. Enter promo code BN26 when you book and your discount will be applied after your booking is confirmed. Ts and Cs apply.
| Start Date | End Date | Price p.p. |
|---|---|---|
| * 02/05/2026 | 09/05/2026 | $3,050.00 |
| * 31/05/2026 | 07/06/2026 | $3,050.00 |
| * 29/08/2026 | 05/09/2026 | $3,050.00 |
| * 03/10/2026 | 10/10/2026 | $3,050.00 |
- Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting along the way
- Staying in quality accommodation, with fantastically warm hospitality
- Easing along the rolling hills of the Colli Sienesi
- Riding the stunning UNESCO heritage region of Val d’Orcia
- Stopping off at the lovely San Gimignano and Montalcino
- Chilling out with a post-ride Chianti
Not sure which trip's right for you? Just ask!
Get in touch and we'll help you find your perfect trip.
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Why choose Tuscany for your cycling holiday?
Tuscany offers a perfect blend of stunning landscapes, rich history, and world-renowned cuisine, making it a dream destination for cyclists. Ride through rolling hills, villages and vineyards while soaking in the charm of this iconic Italian region. It’s an unforgettable way to explore Italy’s heart and soul.
Top places for cycling in Tuscany
Tuscany is a cyclist's dream, offering iconic routes through the Chianti vineyards, the rolling hills of Val d’Orcia, and medieval gems like Siena and San Gimignano. Ride along Lucca’s ancient walls. Each route promises stunning landscapes and rich cultural experiences.
Decide how you ride
Tuscany offers something for every cyclist; gravel riders can explore the Strade Bianche either guided or self guided cycling through the wine regions of Tuscany, stopping off for a bit of wine tasting! Road cyclists can take to the road and travel coast to coast from Riccione to Porto Ercole whilst if you prefer something more leisurely we have a range of relaxing leisure trips exploring some of the historic gems of the Italian countryside.
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