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
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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
| Start Date | End Date | Price p.p. |
|---|---|---|
| 25/09/2021 | 01/10/2021 | £1,365.00 |
| 23/04/2022 | 29/04/2022 | £1,365.00 |
| 24/09/2022 | 30/09/2022 | £1,365.00 |
- 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. |
|---|---|---|
| 18/09/2021 | 24/09/2021 | £925.00 |
| 02/10/2021 | 08/10/2021 | £925.00 |
| 14/05/2022 | 20/05/2022 | £925.00 |
| 28/05/2022 | 03/06/2022 | £925.00 |
| 17/09/2022 | 23/09/2022 | £925.00 |
| 01/10/2022 | 07/10/2022 | £925.00 |
Daily departures available. The season prices below are applicable for all start dates between and inclusive of the stated dates.
2021 26 Mar – 30 Oct.
Season 1 – £1095 pp – 08 Apr to 21 Apr, 03 May to 26 Jun, and 02 Sep to 30 Oct
Season 2 – £1350 pp – 26 Mar to 07 Apr, 22 Apr to 02 May, and 27 Jun to 01 Sep.
2022 26 Mar – 30 Oct.
Season 1 – £1095 pp – 26 Mar to 14 Apr, 02 May to 24 Jun, and 04 Sep to 30 Oct
Season 2 – £1350 pp – 15 Apr to 01 May, and 25 Jun to 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. |
|---|---|---|
| 11/09/2021 | 17/09/2021 | £1,595.00 |
| 28/05/2022 | 03/06/2022 | £1,595.00 |
| 10/09/2022 | 16/09/2022 | £1,595.00 |
- Staying in a Tuscan farmhouse 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 applicable for all start dates between and inclusive of the stated dates.
2021 26 Mar – 30 Oct.
Season 1 – £1160 pp – 08 Apr to 21 Apr, 03 May to 26 Jun, and 02 Sep to 30 Oct
Season 2 – £1325 pp – 26 Mar to 07 Apr, 22 Apr to 02 May, and 27 Jun to 01 Sep.
2022 26 Mar – 30 Oct.
Season 1 – £1160 pp – 26 Mar to 14 Apr, 02 May to 24 Jun, and 04 Sep to 30 Oct
Season 2 – £1325 pp – 15 Apr to 01 May, and 25 Jun to 03 Sep
- Stay in a Tuscan farmhouses overlooking stunning landscapes
- Ride The Montagnola trails, location of a well-known Sienese MTB race
- Sample the best wines of Chianti, Montepulciano and Montalcino
- Riding down the “Crete Senesi” on a roller coaster ridge ride
- Enjoy the journey across Tuscany on a variety of terrain
- Visit the famous hilltop towns of San Gimignano, Monteriggioni, San Quirico d‘Orcia, Pienza
Tuscany - Pisa to Florence
Self-Guided Leisure Cycling Holiday
| Start Date | End Date | Price p.p. |
|---|---|---|
| 11/09/2021 Contact Us | 18/09/2021 | £820.00 |
| 25/09/2021 | 02/10/2021 | £820.00 |
| 07/05/2022 | 14/05/2022 | £820.00 |
| 21/05/2022 | 28/05/2022 | £820.00 |
| 10/09/2022 | 17/09/2022 | £820.00 |
| 24/09/2022 | 01/10/2022 | £820.00 |
Daily departures available. The season prices below are applicable for all start dates between and inclusive of the stated dates.
2021 26 Mar – 30 Oct.
Season 1 – £1010 pp – 08 Apr to 21 Apr, 03 May to 26 Jun, and 02 Sep to 30 Oct
Season 2 – £1170 pp – 26 Mar to 07 Apr, 22 Apr to 02 May, and 27 Jun to 01 Sep.
2022 26 Mar – 30 Oct.
Season 1 – £1010 pp – 26 Mar to 14 Apr, 02 May to 24 Jun, and 04 Sep to 30 Oct
Season 2 – £1170 pp – 15 Apr to 01 May, and 25 Jun to 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
Via Francigena (Tuscany to Rome)
Guided Electric Bike Holiday
| Start Date | End Date | Price p.p. |
|---|---|---|
| 28/08/2021 | 04/09/2021 | £1,545.00 |
| 11/06/2022 | 18/06/2022 | £1,545.00 |
| 27/08/2022 | 03/09/2022 | £1,545.00 |
- 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 amphitheater
- The sense of achievement riding into St Peter’s Square in Rome
Via Francigena - Tuscany to Rome
Guided Mountain Bike Holiday
| Start Date | End Date | Price p.p. |
|---|---|---|
| 02/10/2021 | 09/10/2021 | £1,685.00 |
| 16/04/2022 | 23/04/2022 | £1,685.00 |
| 01/10/2022 | 08/10/2022 | £1,685.00 |
- 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