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.
.png)
Destinations (1)
Types of Cycling / Grades (7)
Departure Month
Level of Support
Destinations (1)
Types of Cycling / Grades (7)
Departure Month
Level of Support
Select Order
Order By
Guided
Tuscany - Strade Bianche Explorer
Guided Gravel Riding Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 10/05/2025 | 17/05/2025 | $2,900.00 |
| 20/09/2025 | 27/09/2025 | $2,900.00 |
- 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
$2,275 P.P.
Grade 3-4 : Moderate/Active
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 – $2275 24 Mar – 16 Jun and 03 Sep – 29 Oct
Season 2 – $2560 17 Jun – 30 Jun and 01 – 02 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 Sienesi’
- Chilling out with a post-ride Chianti or Brunello
Guided
Tuscany - Sacred Routes
Guided Mountain Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 17/05/2025 | 23/05/2025 | $2,805.00 |
| 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. |
|---|---|---|
| 17/05/2025 Last Spaces | 25/05/2025 | $3,480.00 |
| 07/06/2025 | 15/06/2025 | $3,575.00 |
| 13/09/2025 | 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 tour with us.
| Start Date | End Date | Price p.p. |
|---|---|---|
| 24/05/2025 Guaranteed | 31/05/2025 | $3,050.00 |
| 13/09/2025 | 20/09/2025 | $3,050.00 |
- 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 – $2275 24 Mar – 16 Jun and 03 Sep – 29 Oct
Season 2 – $2615 17 Jun – 30 Jun and 01 – 02 Sep
- 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
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 – $1990 17 – 30 Jun and 01 – 02 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 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
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 – $1420 24 Mar – 16 Jun and 03 Sep – 29 Oct
Season 2 – $2140 17 Jun – 30 Jun and 01 – 02 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.
- 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. |
|---|---|---|
| 03/05/2025 | 10/05/2025 | $2,765.00 |
| 31/05/2025 | 07/06/2025 | $2,765.00 |
| 30/08/2025 | 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
You might also like...
News, Reviews & Stories
The Story Behind Sardinia Cape to Cape
Exploring Sardinia's incredible off road gravel trails on our unique Cape to Cape adventure.
Meet our local partners in Prosecco
Discover the story behind our new Italian holidays and meet Giovanni, your expert on the local Prosecco region...