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 7 Holidays in your search for:
- In Cycling Holidays 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
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 - Sacred Routes
Guided Mountain Bike Holiday
| Start Date | End Date | Price p.p. |
|---|---|---|
| 03/06/2023 | 09/06/2023 | £1,825.00 |
| 23/09/2023 | 29/09/2023 | £1,825.00 |
- 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
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.
2022 26 Mar – 30 Oct
Season 1 – £1270 26 Mar – 14 Apr, 02 May – 24 Jun and 04 Sep – 30 Oct
Season 2 – £1420 15 Apr – 01 May and 25 Jun to 03 Sep
2023 25 Mar – 30 Oct
Season 1 – £1360 25 Mar – 05 Apr, 15 Apr – 17 Jun and 04 Sep – 30 Oct
Season 2 – £1520 06 Apr – 14 Apr and 18 Jun – 03 Sep
- 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
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
Tuscany to Rome
Guided Mountain Bike Holiday
| Start Date | End Date | Price p.p. |
|---|---|---|
| 20/05/2023 | 27/05/2023 | £1,795.00 |
| 09/09/2023 | 16/09/2023 | £1,795.00 |
- 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