A 5-day gravel escape around Siena, riding the iconic Strade Bianche through Chianti, Val d’Orcia, and Tuscany’s hilltop towns.

Starting and finishing in the UNESCO World Heritage town of Siena, this 5-day gravel bike tour introduces you to some of the very best Strade Bianche in Tuscany. Overnight stays include Gaiole, the sacred home of the Eroica vintage bike event, as well as the picturesque hilltop towns of Asciano and Pienza—so you can enjoy the post-ride experience just as much as the rides themselves.

We’ve hand-picked exceptional accommodations for this journey, from historic castles to charming agriturismi. Along the way, you’ll ride many of the most iconic gravel sectors featured in the Eroica and Strade Bianche routes, and explore Tuscany’s renowned wine regions, including Chianti and Brunello di Montalcino. Immerse yourself in the culture, cuisine, and scenery that make Tuscany a must-visit destination for gravel cyclists the world over.

• All transfers, incl. pick-up from and drop-off to the airport
• 4 nights accommodation in select boutique accommodations including breakfast
• Support with set-up of rental bike, or assembly/disassembly of own bike
• Daily CyclingHero van support with refreshments and snacks
• Daily multiple route options
• Exclusive access to the CyclingHero Companion App with local insights
• Bike box storage for the entire duration of the trip

Full details of payment instalments are displayed when you select your package.

We understand that unexpected things can come up. That's why we have a flexible and transparent cancellation policy.

For regular departures:

-More than 60 days prior to the departure - Full balance net of deposit refunded -Between 60 and 15 days prior to departure – Any amount paid will be credited towards a future trip within two years -less than 15 days of departure - no refund or credit can be applied For special departures (custom trips & special event departures, i.e. Maratona dles Dolomites):

-More than 120 days prior to the departure - Full balance net of deposit refunded -Between 120 and 60 days prior to the departure - Any amount paid will be credited towards a future trip within two years -Less than 60 prior to the departure - no refund or credit can be applied