Join us on two wheels in Tuscany with one of our Tuscany bike tours and experience one of the true cycling classics! Riders 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. Tuscany really is one of those must-visit destinations that is best explored by bike. With both guided and self-guided bicycle tours in Tuscany on offer, you can enjoy this stunning part of Italy your way.
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Destinations (1)
Types of Cycling / Grades (7)
Departure Month
Level of Support
Destinations (1)
Types of Cycling / Grades (7)
Departure Month
Level of Support
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Guided
Tuscany - Strade Bianche Explorer
Guided Gravel Riding Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 20/09/2025 | 27/09/2025 | $2,845.00 |
- Riding some of the classic “Strade Bianche” of Tuscany as well as lesser-known gravel routes
- Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting
- Exploring the region on a mix of terrains
- Riding the stunning UNESCO heritage region of Val d’Orcia
- Relaxing in small villages for a coffee with the locals
- Easing along the rolling hills of the ‘Colli Sienesi’
- Chilling out with a post-ride Chianti or Brunello
Self-Guided
Self-Guided
Italy
Strade Bianche Explorer
Self-Guided Gravel Bike Tour
Duration
8 daysPrices from
$2,355 P.P.
Grade 3-4 : Moderate/Chellenging
Strade Bianche Explorer
Self-Guided Gravel 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.
2025 24 Mar – 29 Oct (excluding dates throughout July and August)
Season 1 – $2355 24 Mar – 16 Jun and 03 Sep – 29 Oct
Season 2 – $2640 17 Jun – 30 Jun and 01 – 02 Sep
2026 29 Mar – 26 Oct (excluding dates throughout July and August)
Season 1 – $2480 29 Mar – 14 Jun and 09 Sep – 26 Oct
Season 2 – $2775 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.
- Riding some of the classic “Strade Bianche” of Tuscany as well as lesser-known gravel routes
- Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting
- Exploring the region on a mix of terrains
- Riding the stunning UNESCO heritage region of Val d’Orcia
- Relaxing in small villages for a coffee with the locals
- Easing along the rolling hills of the ‘Colli Senesi’
- Chilling out with a post-ride Chianti or Brunello
Guided
Tuscany - Sacred Routes
Guided Mountain Bike Tour
E-MTB HIRE AVAILABLE
This holiday is great fun on a regular mountain bike or an e-mountain bike and you can choose to hire either when you book your holiday with us! If you’re an experienced rider, you can choose one of our quality e-mountain hire bikes and experience the buzz of a pedal-assisted ride. Select your e-MTB hire when you book a holiday with us. Bear in mind that the pace will be set to riders with a regular mountain bike.
| Start Date | End Date | Price p.p. |
|---|---|---|
| 06/09/2025 | 12/09/2025 | $2,805.00 |
- Staying in lovely Tuscan accommodation overlooking stunning landscapes
- Riding the Montagnola trails, the location of a well-known Sienese MTB race
- Sampling the best wines of Chianti, Montepulciano and Montalcino
- Riding down the Crete Senesi on a roller-coaster ridge ride
- Enjoying the journey across Tuscany on a variety of terrain
- Visiting the famous hilltop towns of San Gimignano, Monteriggioni, San Quirico d‘Orcia and Pienza
Guided
Coast to Coast - L'Adriatico al Tirreno
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 13/09/2025 Guaranteed | 21/09/2025 | $3,480.00 |
- 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
Guided
Tuscany to Rome
Guided Electric Bike Tour
E-BIKE TOUR
This holiday has been designed as an e-bike tour allowing you to experience more on two wheels whilst riding with like-minded Skedaddlers. Confident cyclists will enjoy the boost from a battery for those cheeky climbs and longer distances. With less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities. Remember to select your e-bike hire when you book your holiday with us.
| Start Date | End Date | Price p.p. |
|---|---|---|
| 13/09/2025 Guaranteed | 20/09/2025 | $3,060.00 |
- Staying in Tuscan accommodation overlooking stunning landscapes
- Discovering the amazing towns of Siena, San Quirico and Pienza
- Sampling the best wines of Chianti, Montepulciano and Montalcino
- Enjoying the journey from Tuscany to Rome on a variety of terrain, including ancient Roman roads
- Exploring the lesser-known historical towns of Lazio, such as Sutri with it’s Roman amphitheatre
- The sense of achievement riding into St Peter’s Square in Rome
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.
2025 24 Mar – 29 Oct (excluding dates throughout July and August)
Season 1 – $2205 24 Mar – 16 Jun and 03 Sep – 29 Oct
Season 2 – $2615 17 Jun – 30 Jun and 01 – 02 Sep
2026 29 Mar – 26 Oct (excluding dates in July and August)
Season 1 – $2300 29 Mar – 14 Jun and 09 Sep – 26 Oct
Season 2 – $2750 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
Self-Guided
Tuscany - Pisa to Florence
Self-Guided Leisure Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 16/09/2025 Guaranteed | 23/09/2025 | $1,595.00 |
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
2025 24 Mar – 29 Oct (excluding dates throughout July and August)
Season 1 – $1760 24 Mar – 16 Jun and 03 Sep – 29 Oct
Season 2 – $2015 17 – 30 Jun and 01 – 02 Sep
2026 29 Mar – 26 Oct (excluding dates throughout July and August)
Season 1 – $1855 29 Mar – 14 Jun and 09 Sep – 26 Oct
Season 2 – $2125 15 – 30 Jun and 01 – 08 Sep
Alternatively for a great value holiday select one of our scheduled departures below.
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.
- Riding between two of Italy’s most iconic cities
- Exploring Pisa, home of the world-famous Piazza dei Miracoli
- Cycling along quiet country lanes through Tuscan countryside
- Cycling past fairy tale Renaissance palaces and villas
- Visiting Vinci, the birthplace of Leonardo da Vinci
- Spending a free day in Florence, the birthplace of the Renaissance
Self-Guided
Classic Tuscany
Self-Guided Leisure Bike Tour
E-BIKE HIRE AVAILABLE
This tour is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your tour with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities. You may choose to hire an e-bike on a group or supported tour but bear in mind that the pace will be set to riders without an e-bike.
| Start Date | End Date | Price p.p. |
|---|---|---|
| 28/09/2025 | 04/10/2025 | $1,625.00 |
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
2025 24 Mar – 29 Oct (excluding dates throughout July and August)
Season 1 – $1815 24 Mar – 16 Jun and 03 Sep – 29 Oct
Season 2 – $2140 17 Jun – 30 Jun and 01 – 02 Sep
Alternatively, for a great value holiday, please select one of our scheduled departures below.
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.
- Staying at Tuscan farms overlooking stunning countryside
- Visiting the famous towns of Monteriggioni, Radda in Chianti and Siena
- Riding through wonderful landscapes, wide open fields, cypress-lined hills and vineyards
- Trying delicious, regional dishes
- Sampling the best wines of Chianti, Montepulciano and Montalcino
- Absorbing the atmosphere of San Gimignano – a UNESCO World Heritage Site
Guided
Tuscany - Giro della Toscana
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| * 30/08/2025 Fully Booked | 06/09/2025 | $2,765.00 |
- 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
About our Bike Tours in Tuscany
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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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