Three Heroic Days: Where History Meets Gravel
Itinerary
Discover the soul of Tuscany on an unforgettable three-day ride through the iconic strade bianche of L’Eroica. Starting in Gaiole in Chianti, the birthplace of heroic cycling, you’ll traverse vineyard-lined hills, historic castles, and timeless villages.
Cycle past the majestic Brolio Castle, reach the medieval heart of Siena, and conquer the legendary climbs of Castiglion del Bosco en route to Montalcino, land of Brunello wines.
Your final stage takes on the epic Monte Santa Marie, one of cycling’s most revered gravel sections, before rolling through Vagliagli and Radda in Chianti, returning to Gaiole for a well-earned celebration.
More than a ride, this is a journey through landscapes, flavors, and stories that define Tuscany—where every kilometer is steeped in cycling heritage, tradition, and beauty.
Highlights
-
Ride the Legendary White Roads of L’Eroica
-
Explore the Heart of Authentic Tuscany
-
Conquer Epic Climbs and Stunning Vistas
-
Savor Tuscany’s Finest Wines and Cuisine
-
Discover Cycling’s Spiritual Home
-
Experience the Soul of Tuscany from Castles to Brunello Hills
Day 1 – Arrival in Gaiole in Chianti
Arrive in the charming village of Gaiole in Chianti, the heart of Tuscany and birthplace of L’Eroica. Settle into your accommodations and take some time to relax after your journey. In the evening, you may choose to enjoy a leisurely dinner at a local trattoria, savoring traditional Tuscan cuisine paired with fine Chianti wines. It’s the perfect way to begin your Tuscan adventure, immersing yourself in local flavors before the cycling journey begins.
L'Eroico
Level 1 - Very easy
-
Activity
Relax & DiscoverDay 2 - Gaiole to Buonconvento
Begin your adventure in Gaiole in Chianti, birthplace of L’Eroica. Ride through the heart of Tuscany along scenic vineyards and white gravel roads, passing landmarks like Castello di Brolio and stopping at the iconic Bar Eroica. The route continues through rolling hills and historic villages, with highlights including the beauty of Siena, before finishing in the charming village of Buonconvento.
A perfect blend of cycling, history, and Tuscan landscapes, ending with time to relax and enjoy the local atmosphere.
Hotel Ghibellino
Level 3 - Moderate
45Miles | +3435ft | 37% Gravel 63% Road
Activity
Biking
Day 3 - Buonconvento to Asciano & Tuscan Cooking Class
This scenic ride begins in Buonconvento and follows the iconic white roads of L’Eroica, crossing the historic landscapes of Castiglion del Bosco and climbing toward Montalcino, renowned for its Brunello wines. The route then rolls through cypress-lined hills and open countryside before reaching the peaceful village of Asciano. In the afternoon, take part in a Tuscan cooking class followed by dinner, an ideal way to unwind and enjoy the authentic flavors of the region after a rewarding day on the bike.
Agriturismo Il Molinello
Level 4 - Challenging
54Miles | +15394ft | 56% Gravel 44% Road
Activity
BikingDay 4 - Asciano to Gaiole
Set out from Asciano and tackle the legendary Monte Santa Marie, one of the most iconic gravel sectors of L’Eroica. Surrounded by rolling hills and remote countryside, the route winds through the stunning strade bianche and passes the charming villages of Castelnuovo Berardenga, Pianella, and Vagliagli.
The ride then climbs toward Radda in Chianti before the final stretch leads you to Gaiole in Chianti, where your journey concludes in the heart of Tuscan cycling heritage.
L'Eroico
Level 3 - Moderate
43Miles | +4288ft| 43% Gravel 57% Road
Activity
Biking
Day 5 - Echoes of Tuscany: A Day of Rest and Reflection
With the riding complete, this final day invites you to slow down and savor all that you’ve experienced. Take time to enjoy the warm Tuscan sun, share stories with your fellow riders, and reflect on the white roads, hilltop villages, and unforgettable moments that defined your journey. It’s a quiet celebration and the perfect way to let the spirit of Tuscany stay with you long after the ride has ended.
Level 1 - Very easy
Activity
Relax & DiscoverTrip wows
Ride the legendary white roads of L’Eroica through the heart of Tuscany. Conquer iconic climbs, explore medieval villages, and taste world-class wines in the lands of Chianti and Brunello. From Gaiole to Montalcino, each stage blends cycling heritage, breathtaking landscapes, and authentic Tuscan flavors — a true pilgrimage for passionate riders.
Ride Through Cycling Legends
Embark on an unforgettable journey through L’Eroica’s iconic white gravel roads. Pedal past medieval castles and centuries-old vineyards where the spirit of heroic cycling lives on, surrounded by Tuscany’s breathtaking landscapes.
Conquer Iconic Tuscan Climbs
Take on some of Italy’s most legendary cycling climbs, traversing remote roads steeped in history. Feel the thrill of riding the same paths that inspired cycling legends, all while soaking in stunning views of rolling hills and prestigious vineyards.
hotels
Please note that accommodations may vary based on availability.
L'Eroico
L'Eroico in Gaiole in Chianti offers a delightful blend of modern comfort and Tuscan charm. Situated in the heart of Chianti, this intimate B&B provides soundproofed rooms with air conditioning, free Wi-Fi, and satellite TV. Guests can enjoy a delicious breakfast featuring homemade pastries and cakes. Ideal for cyclists, the property offers secure storage for bikes and e-bikes, making it a perfect base for exploring the scenic Eroica routes!
Hotel level
Quality
Plus
Parking
Hotel Ghibellino
Located in the heart of Buonconvento, Hotel Ghibellino is a family-run hotel offering a warm blend of traditional charm and modern comfort. Perfect for cyclists and travelers exploring the Crete Senesi or Via Francigena, the hotel provides secure bike storage, e-bike charging, and a generous breakfast buffet. Guests can relax on the rooftop terrace, enjoy the on-site bar, and dine at the nearby family-owned restaurant. With friendly service and an ideal location near Siena, Montalcino, and Pienza, Hotel Ghibellino is a comfortable base for discovering Tuscany.
Hotel level
Quality
Plus
Parking
Agriturismo Il Molinello
Agriturismo Il Molinello is a family-run farmhouse set in the heart of the Crete Senesi. Housed in a restored 14th-century mill, it offers charming apartments and rooms with rustic style and modern comforts. Guests can enjoy a pool, gardens, and local organic products like olive oil and truffles. Perfect for cyclists and nature lovers, Il Molinello combines authentic Tuscan hospitality with access to some of the region’s most scenic landscapes.
Hotel level
Quality
Plus
Pool, ParkingImportant info
- 4 nights accommodation in charming hotels or guesthouses (double occupancy)
- 4 breakfasts, 1 dinner featuring local cuisine
- Living Roads Kit: cycling cap and water bottle
- Helmet, Pedals and all necessary chargers and pump
- Daily luggage transfer between accommodations
- Detailed GPS routes
- Welcome briefing and orientation by a local representative
- Emergency phone support during the tour
- Secure bike storage at each overnight location
- Access to the Ride with GPS navigation app
- E-bike or premium road bike rental included for the entire tour (feel free to bring your own bike if you prefer)
- Wine tasting at a selected winery
- Tuscan cooking class in the heart of the Chianti countryside
- Private guide for the entire duration of the tour
- Single room supplement
- E-Bikes supplement
- Additional gears
- Travel insurance (highly recommended). See our protection plan here.
- Airfare or transportation to/from the tour start and end locations
- Private transfer on first and last day from/to the nearest train station or airport
- Lunches and dinners not specified in the inclusions
- Personal expenses (e.g., souvenirs, drinks, snacks)
- Optional activities or excursions not mentioned in the itinerary
- Gratuities for drivers or hotel staff
- Additional nights of accommodation before or after the tour dates
-
Included
- 4 nights accommodation in charming hotels or guesthouses (double occupancy)
- 4 breakfasts, 1 dinner featuring local cuisine
- Living Roads Kit: cycling cap and water bottle
- Helmet, Pedals and all necessary chargers and pump
- Daily luggage transfer between accommodations
- Detailed GPS routes
- Welcome briefing and orientation by a local representative
- Emergency phone support during the tour
- Secure bike storage at each overnight location
- Access to the Ride with GPS navigation app
- E-bike or premium road bike rental included for the entire tour (feel free to bring your own bike if you prefer)
- Wine tasting at a selected winery
- Tuscan cooking class in the heart of the Chianti countryside
Not included
- Private guide for the entire duration of the tour
- Single room supplement
- E-Bikes supplement
- Additional gears
- Travel insurance (highly recommended). See our protection plan here.
- Airfare or transportation to/from the tour start and end locations
- Private transfer on first and last day from/to the nearest train station or airport
- Lunches and dinners not specified in the inclusions
- Personal expenses (e.g., souvenirs, drinks, snacks)
- Optional activities or excursions not mentioned in the itinerary
- Gratuities for drivers or hotel staff
- Additional nights of accommodation before or after the tour dates
-
You’ll receive detailed GPS routes, accommodation info, and remote support. Follow the route at your own pace, with full independence but peace of mind.
Our tours range from easy to moderate and are suitable for a wide range of fitness levels. You don’t need to be an athlete, whether you’re a beginner or a more experienced cyclist or hiker, we have options tailored to your ability and pace. E-bike rentals are also available for extra comfort on selected routes. Not sure which adventure suits you best? Check out our Activity Levels to find your perfect fit.
Yes, you’re welcome to use your own bike. It must be in excellent mechanical condition and suitable for the route you’ve chosen. For safety and logistical reasons, we kindly ask you to contact us in advance to confirm whether we can accommodate the transport and storage of your bike before completing your booking.
Trips can be booked exclusively by contacting our team directly. We’re happy to assist you via email or phone and will guide you through every step of the booking process.
Gallery
Get in touch with us
Where would you like to go?
Why Living Roads?
OUR LOCAL TOUCH
As locals, we create journeys inspired by the way we live. Enjoy the best of Italian Roads and Hospitality with our expertise of more than 50 years as a tour operator.
FOR EVERYONE
Our tours are open to everyone, with different levels of difficulty. They’re never meant to be a race, but rather a chance to embrace the slow joy of discovery.
Culture you can taste
Cycling means earning every view and every bite. Our tours include regional wine tastings, cooking class, countryside dinners, and food experiences you’ll remember forever.
CURATED ACCOMODATIONS
Our selection of hotels is guided by the desire to promote local businesses and historic palaces or buildings, creating the perfect blend of authenticity and charm.
ASSISTANCE
You’ll never be alone on the road. You can always count on our remote support during the Self-Guided tours, or on the expertise of our local guides during the guided or joinable tours.
Meaningful miles
We ride slow and smart: our tours are designed to support local communities and reduce environmental impact for a way of traveling that feels as good as it looks.