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
Find Your Ride
We found 8 Holidays in your search for:
- In Tuscany
- Leisure Cycling (All Grades), Mountain Biking (All Grades), Road Cycling (All Grades), Family Cycling (All Grades) or Cycling Adventures (All Grades)
Destinations (1)
Types of Cycling / Grades (6)
Departure Month
Level of Support
Destinations (1)
Types of Cycling / Grades (6)
Departure Month
Level of Support
Tuscany to Rome
Guided Mountain Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| * 20/05/2023 | 27/05/2023 | $2,310.00 |
- Superb Tuscan accommodation and classic landscapes
- Sampling the best wines of Chianti and Montepulciano
- Riding the ridge of Creti Senesi
- Roman roads, superb singletrack and forest fun
- Riding all the way to Rome and arriving in St Peter’s Square
Tuscany - Sacred Routes
Guided Mountain Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 03/06/2023 Contact Us | 09/06/2023 | $2,345.00 |
| 23/09/2023 | 29/09/2023 | $2,345.00 |
- 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
Coast to Coast - L'Adriatico al Tirreno
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 20/05/2023 Fully Booked | 28/05/2023 | $2,785.00 |
| 17/06/2023 | 25/06/2023 | $3,005.00 |
| 16/09/2023 | 24/09/2023 | $2,785.00 |
- 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
Tuscany to Rome
Guided Electric Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 10/06/2023 E-Bike Departure Guaranteed | 17/06/2023 | $2,310.00 |
| 26/08/2023 E-Bike Departure | 02/09/2023 | $2,310.00 |
- 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
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.
2023 26 Mar – 30 Oct
Season 1 – $1885 25 Mar – 05 Apr, 15 Apr – 17 Jun and 04 Sep – 30 Oct
Season 2 – $2180 06 Apr – 14 Apr and 18 Jun – 03 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
Tuscany - Pisa to Florence
Self-Guided Leisure Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 29/04/2023 | 06/05/2023 | $1,280.00 |
| 07/10/2023 | 14/10/2023 | $1,280.00 |
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
2023 25 Mar – 30 Oct
Season 1 – $1475 26 Mar – 05 Apr, 15 Apr – 17 Jun and 04 Sep – 30 Oct
Season 2 – $1730 06 Apr – 14 Apr and 18 Jun – 03 Sep
Alternatively for a great value trip 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
Classic Tuscany
Self-Guided Leisure Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 22/04/2023 Guaranteed | 28/04/2023 | $1,345.00 |
| 30/09/2023 | 06/10/2023 | $1,345.00 |
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
2023 25 Mar – 30 Oct
Season 1 – $1540 25 Mar – 05 Apr, 15 Apr – 17 Jun and 04 Sep – 30 Oct
Season 2 – $1910 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 - Giro della Toscana
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 13/05/2023 Guaranteed | 20/05/2023 | $2,310.00 |
| 10/06/2023 | 17/06/2023 | $2,310.00 |
| 09/09/2023 | 16/09/2023 | $2,310.00 |
- 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