Tuscany is one of the most famous regions in Italy, boasting culture, wine, breath taking views and above all, the best road cycling in Europe. Our cycling tours of Tuscany allow you to fully immerse yourself in the region by allowing you to take in these views, sample the local produce and live like a local for your time with us. Explore our fantastic cycling tours in Tuscany today to find your perfect adventure.
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Destinations (1)
Types of Cycling / Grades (1)
Departure Month
Level of Support
Destinations (1)
Types of Cycling / Grades (1)
Departure Month
Level of Support
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Guided
Coast to Coast - L'Adriatico al Tirreno
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 13/09/2025 Guaranteed | 21/09/2025 | $3,480.00 |
- 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
Self-Guided
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.
2025 24 Mar – 29 Oct (excluding dates throughout July and August)
Season 1 – $2205 24 Mar – 16 Jun and 03 Sep – 29 Oct
Season 2 – $2615 17 Jun – 30 Jun and 01 – 02 Sep
2026 29 Mar – 26 Oct (excluding dates in July and August)
Season 1 – $2300 29 Mar – 14 Jun and 09 Sep – 26 Oct
Season 2 – $2750 15 Jun – 30 Jun and 01 – 08 Sep
To ensure you have the best experience possible, we’d recommend travelling in the Spring or in the Autumn. We don’t as standard offer this tour in the hotter, more humid, busier summer months of July and August. If however your dates are set in July or August, please call us for a chat and we’ll do what we can to accommodate you.
- 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
Guided
Tuscany - Giro della Toscana
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| * 30/08/2025 Fully Booked | 06/09/2025 | $2,765.00 |
- 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
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