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
Find Your Ride
We found 3 Holidays in your search for:
- In Destinations, UK, England or 75 more...
- Leisure Cycling (All Grades)
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
Season 1 – £1265 03 Apr – 17 Jun / 04 Sep – 30 Oct
Season 2 – £1495 25 Mar – 02 Apr / 18 Jun – 03 Sep
2025 24 Mar – 29 Oct
Season 1 – £1335 24 Mar – 16 Jun / 03 Sep – 29 Oct
Season 2 – £1575 17 Jun – 02 Sep
No departures in July and August
Alternatively for a great value holiday choose one of our scheduled departures below.
- 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
Season 1 – £1235 03 Apr – 17 Jun and 04 Sep – 30 Oct
Season 2 – £1395 25 Mar – 02 Apr – 14 Apr and 18 Jun – 03 Sep
2025 24 Mar – 29 Oct
Season 1 – £1295 24 Mar – 16 Jun and 03 Sep – 29 Oct
Season 2 – £1465 – 17 Jun – 03 Sep
No departures in July and August
Alternatively for a great value holiday choose one of our scheduled departures below.
- 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. |
---|---|---|
31/08/2024 | 07/09/2024 | £2,095.00 |
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