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.
Cycling Holidays in Tuscany
Classic Tuscany
Self-Guided Leisure Cycling Holiday
![](https://media.skedaddle.com/cdn-cgi/image/quality=50,format=auto/https://www.skedaddle.com/uk/uploadedImages/roundels/templates/EBIKE-HIRE-AVAILABLE-L.png)
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.
Start Date | End Date | Price p.p. |
---|---|---|
05/10/2024 Guaranteed | 11/10/2024 | £1,045.00 |
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
2024 25 Mar – 30 Oct (excluding dates throughout July and August)
Season 1 – £1265 03 Apr – 17 Jun and 04 Sep – 30 Oct
Season 2 – £1495 25 Mar – 02 Apr, 18 Jun – 30 Jun and 01 – 03 Sep
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 choose 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
Tuscany - Pisa to Florence
Self-Guided Leisure Cycling Holiday
![](https://media.skedaddle.com/cdn-cgi/image/quality=50,format=auto/https://www.skedaddle.com/uk/uploadedImages/roundels/templates/EBIKE-HIRE-AVAILABLE-L.png)
E-BIKE HIRE AVAILABLE
This holiday is well-suited to both normal bikes and pedal assist e-bikes and you can choose to hire either when you book your holiday 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.
Start Date | End Date | Price p.p. |
---|---|---|
28/09/2024 | 05/10/2024 | £1,075.00 |
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
2024 25 Mar – 30 Oct (excluding dates throughout July and August)
Season 1 – £1235 03 Apr – 17 Jun and 04 Sep – 30 Oct
Season 2 – £1395 25 Mar – 02 Apr – 14 Apr and 18 – 30 Jun and 01 – 03 Sep
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 – £1465 17 – 30 Jun and 01 – 02 Sep
Alternatively for a great value holiday choose 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
Tuscany to Rome
Guided Electric Bike Holiday
![](https://media.skedaddle.com/cdn-cgi/image/quality=50,format=auto/https://www.skedaddle.com/uk/uploadedImages/roundels/templates/EBIKE-GROUP-TOUR.png)
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. |
---|---|---|
24/05/2025 | 31/05/2025 | £2,245.00 |
13/09/2025 | 20/09/2025 | £2,245.00 |
- 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
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...