Gaiole in Chianti Eroica Self-Guided Bike Tour
For gravel riding enthusiasts, this is Tuscany at its finest. Base yourself in the Chianti hills and ride loops each day that combine world-famous cycling routes with timeless Tuscan culture.
- Iconic white gravel sections from the Eroica and Strade Bianche races
- Loops to Pienza, Montalcino, Siena, and Crete Senesi
- Stay in one boutique hotel with spa comfort each night
- Daily route briefings and luggage support handled for you
- Ride your way – bring your own bike or choose from premium rental options
- Level: Moderate to challenging
- Best time: March to October
Bike Tour Itinerary
Ride the legendary Eroica gravel roads at your own pace. This self-guided bike tour takes you deep into Chianti and Val d’Orcia, tracing the same strade bianche raced by professionals while weaving through medieval towns, vineyards, and UNESCO landscapes.
Meet at Siena Train Station, transfer to Rapolano Terme, and enjoy a bike fitting. Warm-up loop ride introduces you to the rolling countryside.
Cycle gravel sections made famous by the Strade Bianche, then explore Renaissance Pienza with its cobbled streets and gourmet shops.
Ride the iconic climbs of San Martino in Grania and Monte Sante Marie. Pause at the dramatic Site Transitoire sculpture overlooking the lunar-like landscape.
Spin into Montalcino, fortified hill town and home of Brunello. Visit the fortress for sweeping views before relaxing over a wine cellar dinner.
Gravel tracks lead to Siena’s Piazza del Campo for an espresso in the heart of Palio tradition. Return via secondary gravel roads through Chianti.
Breakfast and departure, with transfer back to Siena Train Station.
What’s Included
The Cost Includes
- 5 nights in a boutique hotel with spa amenities
- Daily breakfasts
- Luggage transfers and support
- Daily route briefings (orientation + daily notes)
- Garmin GPS device with preloaded routes
- Transfer to/from Siena Train Station
- Keepsake Bikeriding Tuscany water bottle
- Keepsake Bikeriding Tuscany Jersey
Not Included
- Bike rental (see Bike Rental Options at checkout)
- Local city taxes (typically €2–€4 per person per night)
- Meals and tastings unless specified
Bike Rental Options
Our tours do not include the price of a bike rental. You are welcome to bring your own bike, or we have the following option for the duration of the tour:
- Gravel carbon bike rental €250
Payable at checkout.
Map
Ready to Ride?
From Chianti’s castles to Siena’s medieval streets, this self-guided Eroica gravel tour delivers Tuscany’s most iconic cycling experience. If you have any questions about this trip before you book, feel free to email us or send a quick message on WhatsApp.
