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 10 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
Via Francigena - Tuscany to Rome
Guided Mountain Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 02/10/2021 | 09/10/2021 | $2,190.00 |
- 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. |
|---|---|---|
| 29/05/2021 | 04/06/2021 | $2,075.00 |
| 11/09/2021 | 17/09/2021 | $2,075.00 |
- 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 “Creti 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
Italy
Coast to Coast - L'Adriatico al Tirreno
Guided Road Bike Tour
Duration
9 daysPrices from
$2,375 P.P.
Grade 3: Moderate
Coast to Coast - L'Adriatico al Tirreno
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 15/05/2021 Contact Us | 23/05/2021 | $2,375.00 |
| 19/06/2021 Contact Us | 27/06/2021 | $2,505.00 |
| 18/09/2021 Guaranteed | 26/09/2021 | $2,375.00 |
- 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
Italy
Via Francigena - Tuscany to Rome
Self-Guided Mountain Bike Tour
Duration
8 daysPrices from
$1,750 P.P.
Grade 3 : Moderate
Via Francigena - Tuscany to Rome
Self-Guided Mountain Bike Tour
2021 Daily departures available from 26 Mar to 30 Oct
Season 1 For trips starting between (and inclusive of) 08 Apr to 21 Apr, 03 May to 26 Jun, and 02 Sep to 30 Oct: $1,750 per person
Season 2 For trips starting between (and inclusive of) 26 Mar to 07 Apr, 22 Apr to 02 May and 27 Jun to 01 Sep: $1,920 per person
Contact us on 1-888-414-6437 or email info@skedaddle.com to check availability for your specific date.
- Stay in a genuine Tuscan accommodation overlooking stunning landscapes
- Sample the best wines of Chianti, Montepulciano and Montalcino
- Riding down the “Creti Senesi” on a roller coaster ridge ride
- Enjoy the journey from Tuscany to Rome on a variety of terrain, including ancient Roman roads
- Visit the famous hilltop towns of San Quirico d‘Orcia and Radicofani
- Ride into St Peter’s Square in Rome
Via Francigena (Tuscany to Rome)
Guided Electric Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 12/06/2021 | 19/06/2021 | $2,010.00 |
| 28/08/2021 | 04/09/2021 | $2,010.00 |
- 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
Tuscany - Pisa to Florence
Self-Guided Leisure Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 08/05/2021 | 15/05/2021 | $1,070.00 |
| 22/05/2021 | 29/05/2021 | $1,070.00 |
| 11/09/2021 | 18/09/2021 | $1,070.00 |
| 25/09/2021 | 02/10/2021 | $1,070.00 |
2021 Daily departures available from 26 Mar – 30 Oct.
Season 1: For trips starting between (and inclusive of) 08 Apr and 21 Apr, 03 May and 26 Jun, or 02 Sep and 30 Oct: $1315 per person.
Season 2: For trips starting between (and inclusive of) 26 Mar and 07 Apr, 22 Apr and 02 May, or 27 Jun and 01 Sep: $1525 per person.
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
Classic Tuscany
Self-Guided Leisure Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 15/05/2021 | 21/05/2021 | $1,205.00 |
| 29/05/2021 | 04/06/2021 | $1,205.00 |
| 18/09/2021 | 24/09/2021 | $1,205.00 |
| 02/10/2021 | 08/10/2021 | $1,205.00 |
2021 Daily departures available from 26 Mar – 30 Oct.
Season 1: For trips starting between (and inclusive of) 08 Apr and 21 Apr, 03 May and 26 Jun, or 02 Sep and 30 Oct: $1425 pp.
Season 2: For trips starting between (and inclusive of) 26 Mar and 07 Apr, 22 Apr and 02 May, or 27 Jun and 01 Sep: $1755 pp.
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
A Taste of Tuscany
Guided Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 24/04/2021 | 30/04/2021 | $1,780.00 |
| 25/09/2021 | 01/10/2021 | $1,780.00 |
- 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
Tuscany - Giro della Toscana
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 22/05/2021 | 29/05/2021 | $2,050.00 |
| 12/06/2021 Guaranteed | 19/06/2021 | $2,050.00 |
| 11/09/2021 | 18/09/2021 | $2,050.00 |
- 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
Tuscany - Giro della Toscana
Self-Guided Road Bike Tour
2021 Daily departures available from 26 Mar to 30 Oct.
Season 1 For trips starting between (and inclusive of) 08 Apr to 21 Apr, 03 May to 26 May, and 02 Sep to 30 Oct: $1,680 per person
Season 2 For trips starting between (and inclusive of) 26 Mar to 07 Apr, 22 Apr to 02 May, and 27 Jun to 01 Sep: $2,010 per person
Contact us on 1-888-414-6437 or email info@skedaddle.com to check availability for your specific date.
Hotel upgrade option applies to 4 out of 7 nights – San Gimignano, Radda in Chianti, Pienza & Montalcino.
- 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