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.
25 Years of Pedallin' Passion
Cycling Holidays in Tuscany
Find Your Ride
We found 4 Holidays in your search for:
- In Cycling Holidays in Tuscany
- Leisure Cycling (All Grades)
Destinations (1)
Types of Cycling / Grades (1)
Departure Month
Level of Support
Destinations (1)
Types of Cycling / Grades (1)
Departure Month
Level of Support
A Taste of Tuscany
Guided Cycling Holiday
- Visiting the famous towns of Volterra, San Gimignano, Monteriggioni, Radda in Chianti and Siena
- Riding through wonderful landscapes, wide open fields, cypress-lined hills and vineyards
- Tasting delicious regional culinary specialities
- Sampling the best wines of Chianti, Montepulciano and Montalcino
- Experiencing Italian culture at its finest
- Having an afternoon aperitivo in Piazza del Campo in Siena
Classic Tuscany
Self-Guided Leisure Cycling Holiday
| Start Date | End Date | Price p.p. |
|---|---|---|
| 01/10/2022 Guaranteed | 07/10/2022 | £990.00 |
| 22/04/2023 | 29/04/2023 | £1,045.00 |
| 30/09/2023 | 07/10/2023 | £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.
2022 26 Mar – 30 Oct
Season 1 – £1175 26 Mar – 14 Apr, 02 May – 24 Jun and 04 Sep – 30 Oct
Season 2 – £1445 15 Apr – 01 May and 25 Jun – 03 Sep
2023 26 Mar – 30 Oct
Season 1 – £1195 25 Mar – 05 Apr, 15 Apr – 17 Jun and 04 Sep – 30 Oct
Season 2 – £1485 06 Apr – 14 Apr and 18 Jun – 03 Sep
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
| Start Date | End Date | Price p.p. |
|---|---|---|
| 29/04/2023 | 06/05/2023 | £995.00 |
| 07/10/2023 | 14/10/2023 | £995.00 |
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
2022 26 Mar – 30 Oct
Season 1 – £1130 26 Mar – 14 Apr, 02 May – 24 Jun and 04 Sep – 30 Oct
Season 2 – £1395 15 Apr – 01 May and 25 Jun – 03 Sep
2023 25 Mar – 30 Oct
Season 1 – £1145 25 Mar – 05 Apr, 15 Apr – 17 Jun and 04 Sep – 30 Oct
Season 2 – £1395 06 Apr – 14 Apr and 18 Jun – 03 Sep
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
| Start Date | End Date | Price p.p. |
|---|---|---|
| 10/06/2023 | 17/06/2023 | £1,795.00 |
| 26/08/2023 | 02/09/2023 | £1,795.00 |
- 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