Tuscan Gravel Legends: The Most Epic Routes Become One
Itinerary
This eight-day cycling journey weaves through Tuscany’s most enchanting landscapes, from the legendary white roads of L'Eroica in Gaiole to the ancient fortress of Radicofani. Pedal through the mystical tufa lands, discovering cliffside villages like Pitigliano, then immerse yourself in the wild beauty of Maremma. Cycle along the serene Tyrrhenian coast and reflect at the roofless Abbey of San Galgano. Follow the ancient Via Francigena to the fairytale fortress of Monteriggioni, before returning to Gaiole, where Tuscany’s timeless beauty and history become part of you.
Highlights
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Ride the White Roads of L’Eroica in Gaiole in Chianti
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Climb to Radicofani’s Ancient Hilltop Fortress
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Explore Tufa Landscapes and Cliffside Villages
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Cycle Across the Wild Maremma to the Tyrrhenian Coast
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Discover San Galgano Abbey and the Sword in the Stone
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Follow the Via Francigena to Monteriggioni Fortress
Day 1 - Gaiole Loop Warm up Ride
Your adventure begins in Gaiole in Chianti, the birthplace of L'Eroica, where the spirit of vintage cycling comes alive. Today serves as a warm-up to help you adjust to your bike and immerse yourself in the stunning Chianti landscape. The day’s ride takes you on the famed ascent to Badia Coltibuono, a renowned climb with smooth switchbacks that wind through the rolling hills of Chianti. After reaching the summit, enjoy the scenic route toward Radda, followed by a thrilling descent with sweeping hairpin turns on pristine asphalt. It’s the perfect opportunity to build confidence before tomorrow's grand cycling adventure. Afterward, return to Gaiole for a well-deserved dinner and rest, gearing up for the journey ahead.
Paradiso in Chianti
Level 1 - Very easy
19Km
Activity
BikingDay 2 - Gaiole in Chianti to Buonconvento
Today, you'll ride some of L'Eroica’s most iconic routes, starting with a smooth descent from Gaiole towards Madonna a Brolio, where a quick coffee at the Eroica Café fuels you up for the day. Your first gravel section takes you past vineyards and stunning views of Brolio Castle, a symbol of Tuscany’s rich cycling and wine heritage. After navigating scenic hairpin turns, you’ll ride along ridge roads with views of hilltop villages, eventually reaching the historic center of Siena, where you'll walk your bike through the famous Piazza del Campo. Continuing through the Eroica Francigena route, tackle rolling hills and gravel paths, with a well-timed stop for lunch in Radi. The day ends with a thrilling descent and a peaceful ride along car-free gravel roads to Buonconvento, where you will enjoy a wine tasting at a selected winery in Buonconvento to celebrate the day’s adventure.
Hotel Ghibellino
Level 4 - Challenging
79Km
Activity
Biking
Day 3 - Buonconvento to Radicofani
Your ride starts from Buonconvento, following historic gravel paths of the Via Francigena and L'Eroica routes. Pedal through quiet villages and cypress-lined roads, entering the UNESCO-listed Val d'Orcia at San Quirico d'Orcia. Stop for a coffee before navigating the gravel roads towards Bagno Vignoni, home to a unique Roman thermal pool. Continue towards Pienza, with a special detour to admire the iconic Chapel of Vitaleta, one of Tuscany's most photographed spots. After lunch in Pienza, stock up on supplies before tackling the challenging climb to Radicofani. At 896 meters, this historic fortress offers panoramic views, rewarding you for conquering the highest point of the day.
Agriturismo La Selvella
Level 4 - Challenging
73Km
Activity
BikingDay 4 - Radicofani to Pitigliano
Get ready for an epic day as you ride through some of Tuscany's most dramatic landscapes! Start with a thrilling gravel descent from Radicofani and enjoy winding roads that take you towards Castell'Azzara. Then, dive into the medieval magic of Sorano, carved into volcanic tufa rock...Tuscany’s own "Matera"! Next, explore the ancient "vie cave," Etruscan roads cut deep into rock, leading you to Sovana, a charming medieval gem with a stunning 12th-century cathedral. Refuel here, as you’ll need it for the journey to Pitigliano, also known as "Little Jerusalem." You’ll arrive via an unforgettable vie cave entrance, climbing steps to reach the cliffside town. End the day in Pitigliano, explore its Jewish ghetto, and savor local specialties while celebrating a ride through Tuscany's rich history and breathtaking landscapes.
Le Camere del Ceccottino
Level 4 - Challenging
69km
Activity
Biking
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Day 5 - Pitigliano to Orbetello
Start your day with a climb from Pitigliano to Manciano, the “Sentinel of the Maremma,” offering sweeping views of the surrounding hills. After a smooth descent, continue through the rolling Maremma countryside towards Pescia Fiorentina or Pescia Romana for a well-deserved coffee or lunch break. Next, head towards the coast and enjoy a short climb to the stunning Feniglia sand bar, a lush reserve of maritime pine forests. Ride along this unique strip of land before reaching Monte Argentario, a former military outpost with a rich history. Finish the day cycling into Orbetello, where you’ll check into your hotel and celebrate a ride that has taken you from the wild heart of Maremma to the sparkling Mediterranean coastline.
Hotel Relais I Presìdi
Level 4 - Challenging
89Km
Activity
BikingDay 6 - Orbetello to PuntaAla Camp & Resort
Pedal out of Orbetello and make your way across the Tuscan landscape, transitioning from busy roads to quiet countryside lanes. Stay alert at the Via Aurelia crossing, then cruise past the Albegna River toward the peaceful village of Alberese...the gateway to the Maremma Natural Park. Here, tradition lives on through the "butteri," Tuscany’s own cowboys. From Alberese, your journey winds toward the coastal gem of Castiglione della Pescaia. Expect a blend of scenic cycle paths and lively roads as you approach this medieval seaside town, known for its historic fortress, charming marina, and inviting lunch spots. The final stretch leads you along tranquil paths and gravel roads to Puntala Camp & Resort, a beachfront retreat nestled in pine forests. Kick back, grab supplies, enjoy a seaside meal, and toast to another rewarding ride along Italy’s sun-soaked coast.
Punt'Ala Camp & Resort
Level 4 - Challenging
78Km
Activity
Biking
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Day 7 - PuntAla Camp & Resort to Palazzetto
Get ready for one of the most breathtaking stretches of the Tuscan coast, starting with Cala Violina, a secluded beach where the sand literally sings beneath your feet. Surrounded by lush Mediterranean scrub and pines, it's a true natural gem. From there, you'll head inland for a steady climb to the quiet village of Tatti, followed by a scenic ride through rolling hills and rustic countryside. A few charming osterias along the way offer a chance to pause and enjoy local flavors! Your day ends in the peaceful hamlet of Palazzetto, a timeless hideaway nestled in Siena's hills. Here, the silence and beauty invite you to slow down and savor Tuscany at its purest.
Il Palazzetto
Level 3 - Moderate
62Km
Activity
BikingDay 8 - Palazzetto to Gaiole in Chianti
Leaving Palazzetto, your journey begins with a magical detour to the roofless Abbey of San Galgano, a soaring Gothic relic open to the sky, steeped in legend and silence. From there, the ride weaves through forests and villages, from the hidden paths of Valle del Merse to the graceful charm of Sovicille. Soon, the towers of Monteriggioni rise on the horizon: an iconic medieval gem frozen in time. As you climb into the heart of Chianti, passing through Castellina and Radda, the landscape opens to vineyards, ancient trails, and the final stretch through Brolio. With each pedal stroke, you trace the soul of Tuscany - its history, flavors, and timeless beauty - all the way back to Gaiole in Chianti.
L'Eroico
Level 4 - Challenging
87Km
Activity
Biking
Day 9 - Echoes of the Ride: A Tuscan Farewell
After eight days of discovery, this final day invites you to slow down and let it all sink in. Sit back under the Tuscan sun, share stories with fellow travelers, and relive the roads, villages, and moments that made this journey unforgettable. It’s a quiet celebration of everything you’ve seen, felt, and accomplished, the perfect way to end your adventure.
Level 1 - Very easy
Activity
Relax & DiscoverTrip wows
Charge through castles, coastlines, and ancient roads on an unforgettable eight-day cycling quest across Tuscany’s most iconic and untamed terrains... from the legendary white gravel of L’Eroica to cliffside villages, sun-drenched shores, and the wild beauty of the Maremma.
Castle Cruising
Glide past the storybook towers of Brolio Castle, where vine-covered walls and centuries of noble history rise from the Chianti hills, and feel like a modern-day knight on two wheels, riding through a landscape steeped in legend and timeless beauty.
Piazza Dreams
Roll into Siena’s stunning Piazza del Campo, where the warm terracotta bricks of one of the world’s most iconic medieval squares radiate with centuries of history, and imagine the roar of crowds during the Palio as you pause beneath the towering Torre del Mangia... soaking in the grandeur, elegance, and timeless spirit of this extraordinary city.
Val d’Orcia Vibes
Cruise through the cinematic beauty of Val d’Orcia, where every curve reveals a new masterpiece—winding roads framed by sculptural cypress trees, undulating golden hills that glow under the Tuscan sun, and perfectly preserved villages perched like jewels on the horizon. This is a landscape that feels both timeless and surreal, celebrated in films, paintings, and poetry, and honored as a UNESCO World Heritage Site. As you pedal through this dreamlike valley, you’ll understand why Val d’Orcia is considered the very soul of Tuscany—where nature, history, and harmony come together in one unforgettable ride.
Abbey in the Sky
Stand in awe at San Galgano Abbey, a mystical, roofless Gothic ruin where sunlight streams through empty window frames, casting shifting patterns on ancient stone. Surrounded by rolling fields and silence, this hauntingly beautiful abbey invites quiet reflection as you wander through its skeletal arches... an unforgettable moment of serenity and wonder in the heart of the Tuscan countryside.
hotels
Please note that accommodations may vary based on availability.
Paradiso in Chianti
Paradiso in Chianti is an elegant, family‑run hotel nestled in the heart of Gaiole in Chianti, Tuscany. Housed in a recently renovated historic palazzo, it blends traditional Tuscan charm with contemporary comfort . The property overlooks the town square and is just steps from local cafés, wine bars, and restaurants — yet offers a peaceful retreat. Paradiso in Chianti is a favorite spot for cyclists on the famed Eroica route!
Hotel level
Quality
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 La Selvella
Agriturismo La Selvella is a beautifully restored 18th-century farmhouse nestled in the hills of Val d’Orcia. Surrounded by organic farmland, olive groves, and vegetable gardens, it offers a peaceful Tuscan escape with elegant rooms, home-cooked meals, and a strong focus on sustainability. Guests enjoy farm-fresh breakfasts, traditional dinners made with local ingredients, a scenic pool, and experiences like cooking classes and truffle hunts. With warm hospitality and stunning views, La Selvella is ideal for travelers seeking authenticity, nature, and relaxation in the heart of Tuscany.
Hotel level
Quality
Plus
Pool, Restaurant.webp)
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Le Camere del Ceccottino
A refined guesthouse on the top floor of a historic 17th-century palazzo in the heart of Pitigliano, overlooking the charming Piazza San Gregorio VII. Featuring five elegantly soundproofed rooms. Ideal for Living Roads guests seeking authentic Tuscan immersion, Le Camere del Ceccottino offers stylish, peaceful accommodations with easy access to local culture, dining, and the medieval streets of Pitigliano.
Hotel level
Quality
Plus
Restaurant, Parking.webp)
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Hotel Relais I Presìdi
Hotel Relais I Presidi is a charming boutique retreat nestled just outside Orbetello, overlooking the tranquil lagoon and lush Maremma countryside. With its welcoming atmosphere and attentive staff, Hotel Relais I Presidi offers a delightful retreat for travelers exploring the Tuscan countryside by bike.
Hotel level
Quality
Punt'Ala Camp & Resort
PuntAla Camp & Resort offers a perfect blend of nature, comfort, and adventure on Tuscany’s stunning coastline. Nestled in a lush pine forest with direct access to a sandy beach, the resort features stylish accommodations, outdoor sports, and family-friendly amenities — all just steps from the sea. Ideal for nature lovers, active travelers, and those seeking a relaxing escape.
Hotel level
Quality
Plus
Restaurant, Parking, Gym
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
ParkingImportant info
- 8 nights accommodation in charming hotels or guesthouses (double occupancy)
- 8 breakfasts and 3 dinners 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 in Buonconvento
- 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
- Transfer on Day 1/Day 5 from/to the nearest train station/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
- 8 nights accommodation in charming hotels or guesthouses (double occupancy)
- 8 breakfasts and 3 dinners 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 in Buonconvento
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
- Transfer on Day 1/Day 5 from/to the nearest train station/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.
We offer high-quality touring bikes, gravel bikes, and e-bikes, depending on the tour itinerary and terrain. All bikes are selected to ensure comfort, performance, and reliability across a variety of landscapes.
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.
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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.