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 some of the best Italian food in all the land on a cycling tour of Tuscany. This is one of those must-visit destinations best explored by bike. Whether you’re after leisurely rides through rolling vineyards, challenging road climbs, or scenic gravel and e-bike adventures, there’s a Tuscany cycling holiday to suit every type of rider. You can enjoy this region on one of our guided or self-guided tours, allowing you to experience Tuscany your own 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
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Top Destinations for Cycling in Tuscany
Tuscany is a world-famous cycling destination, iconic within cycling history, and certain regions stand out for their scenery, routes, and accessibility for different types of riders.
Val d’Orcia – Famous for rolling hills, cypress-lined roads, and picturesque villages, Val d’Orcia is ideal for those seeking leisurely cycling experiences in Tuscany or gentle road rides. Its smooth roads and picturesque landscapes make it perfect for beginners and riders looking for scenic, relaxed days in the saddle.
Chianti Classico – Vineyards, olive groves, and winding country roads define this region. Chianti offers more undulating terrain, making it ideal for confident road cyclists and those seeking a mix of challenge and scenery. Cyclists can stop at local wineries and trattorias, making it a perfect blend of cycling and culture. You’ll see all of this in our Classic Tuscany holiday.
Tuscany Trail – For adventurous riders seeking longer distances and mixed-surface routes, the Tuscany Trail combines road cycling and gravel adventures across the region. It’s ideal for experienced cyclists and those looking to explore beyond the main towns, with rewarding landscapes and varied terrain.
Whether you’re seeking relaxed cycling holidays in Tuscany, scenic road rides, or a multi-day challenge, these destinations showcase why Tuscany is among the world’s most beloved cycling regions.
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Guided
Coast to Coast - L'Adriatico al Tirreno
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 16/05/2026 Guaranteed | 24/05/2026 | $3,850.00 |
| 12/09/2026 Guaranteed | 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 – $2565 29 Mar – 14 Jun and 09 Sep – 26 Oct
Season 2 – $2995 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
| Start Date | End Date | Price p.p. |
|---|---|---|
| 02/05/2026 Guaranteed | 09/05/2026 | $2,995.00 |
| 31/05/2026 | 07/06/2026 | $2,995.00 |
| 29/08/2026 | 05/09/2026 | $2,995.00 |
| 03/10/2026 Guaranteed | 10/10/2026 | $2,995.00 |
- 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.
Key Experiences on Tuscany Cycling Holidays
Tuscany offers far more than scenic roads — it’s a playground for diverse cycling experiences that suit all tastes and abilities. One standout way to cycle Tuscany is on gravel, where you’ll leave the busy roads behind and explore quiet farm tracks, rolling country lanes, and historic paths that wind through vineyards and olive groves. Skedaddle’s gravel-focused Tuscany cycling holidays bring these routes to life, giving you a true sense of the region’s rich landscape and rural charm.
Another increasingly popular option is e-bike touring. Perfect for riders who want to enjoy the scenery with a little extra support, e-bikes let you tackle longer distances and rolling terrain with ease. Glide through Val d’Orcia’s iconic hills, explore the peaceful lanes of Chianti Classico, or take in panoramic views without strain.
For traditional road riders, there are also cycle tour options in Tuscany that combine gentle climbs with cultural stops, local food tastings, and leisurely progress through historic towns.
Whether you’re seeking adventure on gravel, effortless days on an e-bike, a challenging mountain climb, or classic road touring, Tuscany cycling holidays offer unforgettable experiences for every style of rider.
What are the roads like in Tuscany?
Tuscany’s roads are generally quiet and well-maintained, with smooth asphalt on main routes and peaceful, scenic country lanes. The famous ‘white roads’, the Strade Bianche, offer a more rustic gravel experience which is legendary within the world of professional cycling. The rolling Tuscan hills offer rewarding riding for regular cyclists, with quiet paved roads, undulating terrain, and the option to explore off-road gravel paths through vineyards and olive groves.
What’s the weather like?
Tuscany enjoys a mild Mediterranean climate. Spring and early autumn offer ideal cycling conditions, with warm days and cool mornings. Summers can be hot, especially inland, while winter is cooler but manageable. These conditions make Tuscany cycling holidays enjoyable almost year-round, particularly for cyclists who enjoy active days, rolling landscapes, and the reward of exploring by bike.
Cultural insights while cycling in Tuscany
Cycling in Tuscany is as much about the culture as the scenery. Riders pass through medieval towns, historic villas, and bustling piazzas, with chances to sample local wines, olive oils, and regional cuisine. It’s a richly rewarding way to experience Tuscany’s history and atmosphere for cyclists comfortable with rolling terrain.
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