Eroica Roads Gravel Self-Guided Bike Tour
Self-guided gravel bike tour to discover the most beautiful roads of the Eroica.
You’ll start in Siena on the famous dirt roads of the Strade Bianche and the Via Francigena.Over these 5 days, you’ll discover the most beautiful countryside in the province of Siena, with breathtaking, mostly off-road landscapes. The self-guided departure from Siena to Montalcino ends in the Val d’Orcia, a UNESCO World Heritage Site
Bike Tour Itinerary
This Self guided take you in the heart of the Gravel Road of Tuscany. Ride through the vineyards of the Brunello wine, and the amazing landscape of the Crete Senesi.
- Best time: March to October
- Cycling routes through Val d’Orcia, Siena, Chianti and Montalcino
- UNESCO sites including Pienza and Siena
- Thermal spa towns, medieval abbeys, and fortress villages
- Daily luggage transfers and boutique hotel stays
- Ride your way – bring your own bike or choose from premium rental options
- Level: Moderate to challenging
meet and greet at your hotel, bike setup, and test ride.Just outside the center of Siena, you’ll enjoy one of the dirt roads of the Strade Bianche. This is just a taste of the dirt roads we offer on this self-guided bike tour
Today you’ll ride most of the dirt roads of the Eroica, from Siena to Gaiole in Chianti. This small village is a villa in Chianti, famous for being the starting point of the first Eroica in 1997, and today the cycling rally is one of the most famous… be sure to stop in Gaiole to visit the historic “Strade Bianche” shop.
Today we begin with a beautiful descent, along paved and dirt roads, to Buonconvento. From here, you’ll ride 10 km along the Pieve a Salti stage of the Strade Bianche and L’Eroica, to a small village perfect for breakfast with a cappuccino.
From here, you’ll reach Pienza via dirt roads and secondary roads.
Enjoy the Val d’Orcia today! Today you’ll cycle to discover the most beautiful roads and landscapes of this valley, pedaling through San Quirico and Monticchiello. Remember to take a break at the end of the route to enjoy one of the world’s best gelatos! I’ll let you know where!
After breakfast End of your
EROICA ROADS GRAVEL SELF GUIDED BIKE TOUR
What's Included
The Cost Included
- 5 nights in beautiful boutique hotels
- Daily breakfasts
- Luggage transfers between hotels
- Daily route briefings (orientation + daily notes)
- Garmin GPS device with preloaded routes
- Sightseeing, restaurant & shopping suggestions
- Pick-up of bikes and gear in Castellina in Chianti at tour end
- Keepsake Bikeriding Tuscany water bottle
- Keepsake Bikeriding Tuscany jersey
Not Included
- Bike rental (see Bike Rental Options below)
- Local city taxes (typically €2–€4 per person per night)
- Wine tastings and meals unless specified
Bike Rental Option
Our tours do not include the price of a bike rental. You are welcome to bring your own bike, or we have the following options for the duration of the tour:
- Carbon Gravel bike rental €250
- E-Gravel rental €325
Payable at checkout.
Map
Ready to Ride?
From Siena Unesco town to Montalcino, the Brunello wine town, this self guided bike tour gravel cycling you troughs the best gravel roads of Tuscany. From Siena to the Unesco Orcia Valley.If you have any questions about this trip before you book, feel free to email us or send a quick message on WhatsApp.


















