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)
Cycling Holidays in Tuscany
Destinations (81)
Types of Cycling / Grades (7)
Departure Month
Level of Support
Destinations (81)
Types of Cycling / Grades (7)
Departure Month
Level of Support
Select Order
Order By
Self-Guided
Classic Tuscany
Self-Guided Leisure Cycling Holiday
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 | £1,195.00 |
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 – £1335 24 Mar – 16 Jun and 03 Sep – 29 Oct
Season 2 – £1575 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 - Sacred Routes
Guided Mountain Bike Holiday
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 | £2,065.00 |
| 16/05/2026 | 22/05/2026 | £2,175.00 |
| 05/09/2026 | 11/09/2026 | £2,175.00 |
- 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
Self-Guided
Tuscany - Sacred Routes
Self-Guided Mountain Bike Holiday
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 – £1695 24 Mar – 16 Jun and 03 Sep – 29 Oct
Season 2 – £1865 17 Jun – 30 Jun and 01 – 02 Sep
2026 29 Mar – 26 Oct (excluding dates throughout July and August)
Season 1 – £1785 29 Mar – 14 Jun and 09 Sep – 26 Oct
Season 2 – £1965 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.
- 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
Self-Guided
Tuscany - Pisa to Florence
Self-Guided Leisure Cycling Holiday
| Start Date | End Date | Price p.p. |
|---|---|---|
| 16/09/2025 Guaranteed | 23/09/2025 | £1,175.00 |
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 – £1295 24 Mar – 16 Jun and 03 Sep – 29 Oct
Season 2 – £1485 17 – 30 Jun and 01 – 02 Sep
2026 29 Mar – 26 Oct (excluding dates throughout July and August)
Season 1 – £1365 29 Mar – 14 Jun and 09 Sep – 26 Oct
Season 2 – £1565 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
Guided
Tuscany to Rome
Guided Electric Bike Holiday
E-BIKE HOLIDAY
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 Fully Booked | 20/09/2025 | £2,255.00 |
| 23/05/2026 | 30/05/2026 | £2,335.00 |
| 12/09/2026 | 19/09/2026 | £2,335.00 |
- 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
Not sure which trip's right for you? Just ask!
Get in touch and we'll help you find your perfect trip.
News, Reviews & Stories
Charging into the sunset: e-bike holiday
Skedaddle designer Helen Wallis tells us about her experience riding an e-bike through Tuscany...