Chianti Trails: Hiking Through Legendary Vineyards from Radda
Itinerary
Experience the soul of Tuscany on a 3-day hiking journey through Chianti Classico, based in the medieval village of Radda in Chianti. Each day offers a unique loop trail—through historic vineyards, ancient roads, and charming hilltop villages like Volpaia and Lecchi—revealing the hidden beauty and traditions of the region. Along the way, you’ll discover family-run wineries, centuries-old winemaking practices, and sweeping views that capture the essence of the Tuscan countryside. The itinerary blends cultural immersion with outdoor adventure, appealing to both seasoned hikers and casual walkers. Each evening ends with local wine, traditional cuisine, and the warm hospitality of the locals.
Highlights
- Explore the heart of Chianti Classico from the medieval village of Radda in Chianti
- Hike unique daily loops through historic vineyards, ancient roads, and hilltop villages
- Discover charming villages like Volpaia and Lecchi, rich in history and tradition
- Visit family-run wineries and learn centuries-old winemaking practices
- Enjoy sweeping views that capture the beauty of the Tuscan countryside
- End each day with local wine, traditional cuisine, and the warmth of Tuscan hospitality
Day 1 - Volpaia Loop
Step into the heart of Chianti Classico with a hiking adventure that blends centuries of winemaking tradition with the beauty of Tuscany's rolling hills. Based in the medieval town of Radda in Chianti, you'll wander through legendary vineyards, ancient oak forests, and along secluded countryside trails once traveled by wine merchants and nobles. Highlights include visits to historic estates and fairy-tale villages like Volpaia, where medieval architecture and winemaking still go hand in hand. Each day ends back in Radda, where Tuscan hospitality, local wine, and warm village charm offer the perfect close to an unforgettable experience.
Palazzo Leopoldo Dimora Storica & Spa
Level 3 - Moderate
18Km
Activity
HikingDay 2 - Lecchi Loop
Your second day in Chianti invites you on a scenic journey through some of the region’s most peaceful and untouched landscapes. Setting out from Radda, you'll follow age-old trails through vineyards and olive groves, offering a true taste of rural Tuscany far from the tourist crowds. The charming village of Lecchi in Chianti awaits—an authentic, stone-built hamlet that captures the spirit of medieval Tuscany and its deep-rooted traditions. As you return to Radda along a new path, ever-changing views of the Chianti hills ensure your day ends with fresh memories and timeless beauty.
Palazzo Leopoldo Dimora Storica & Spa
Level 5 - Very challenging
29Km
Activity
Hiking
Day 3 - Badia Coltibuono Loop
Day two of your Chianti adventure leads you east from Radda into a landscape rich with history, spirituality, and winemaking heritage. The journey brings you to the magnificent Badia a Coltibuono, a centuries-old abbey that stands as a symbol of Chianti’s deep connection to the land and its traditions. As you continue through rolling hills and vineyard-covered slopes, you’ll pass through charming medieval towns and along the famed white gravel roads that define the region’s rustic beauty. By evening, you return to Radda filled with the stories, sights, and serenity of Tuscany’s timeless countryside.
Palazzo Leopoldo Dimora Storica & Spa
Level 5 - Very challenging
24Km
Activity
HikingDay 4 - Until We Meet Again in Tuscany
After days of exploring Chianti’s vineyards, villages, and timeless trails, the final day is devoted to heartfelt farewells and quiet reflection. It’s a moment to savor the memories made, the friendships formed, and the landscapes that will linger in your mind, while already dreaming of the next adventure that awaits.
Level 1 - Very easy
Activity
Relax & Discover
Hike Through History
Wander along centuries-old white roads and secluded trails that lead deep into the heart of Tuscany’s most storied landscapes. These historic paths, once traveled by merchants, monks, and winemakers, reveal a side of Chianti few visitors ever see. From the hilltop village of Volpaia, where castle walls and stone houses whisper tales of medieval rivalries, to the peaceful borgo of Lecchi, where olive groves and vineyards stretch into the horizon, each step brings you closer to the region’s authentic spirit. This is not just a walk through nature, it’s a journey through time.
Taste the Tradition
At the end of each day's hike, you'll be rewarded with more than just scenic views—you’ll be welcomed into the heart of Chianti’s food and wine culture. Dine in cozy trattorias and family-run wine bars where traditional Tuscan recipes are served with pride and passion. Sip world-class Chianti Classico wines, often made just miles from where you walked that day, and discover the art of pairing local flavors—from handmade pasta and wild boar ragu to pecorino cheese and fresh olive oil. Here, every meal is a celebration of the land, its people, and a centuries-old culinary heritage that continues to thrive.
Sleep in Storybook Tuscany
Your home base in Radda in Chianti offers more than comfort—it offers a sense of timeless wonder. This beautifully preserved medieval village, once the capital of the historic Chianti League, is a quiet haven nestled among vineyards and cypress-lined hills. With its narrow cobblestone streets, stone houses, and panoramic views, Radda feels like a living postcard. After days spent exploring the countryside, return to welcoming hospitality, local wine, and peaceful surroundings that invite you to slow down, breathe deeply, and fully embrace the rhythm of Tuscan life.
hotels
Please note that accommodations may vary based on availability.
Palazzo Leopoldo Dimora Storica & Spa
Palazzo Leopoldo is a historic hotel nestled in the heart of Radda in Chianti. Housed in a 13th-century noble residence once frequented by Grand Duke Leopold II, it seamlessly blends medieval charm with modern luxury. Guests can unwind in elegantly appointed rooms featuring original frescoes and terracotta floors, indulge in traditional Tuscan cuisine at the renowned La Perla del Palazzo restaurant, and rejuvenate at the exclusive Spa Vignavecchia. Whether you're savoring local wines on the panoramic terrace or exploring the picturesque Chianti hills, Palazzo Leopoldo offers an unforgettable Tuscan retreat.
Hotel level
Premium
Plus
SPA, Pool, RestaurantImportant info
- 1 expert guide
- 4 nights accommodation in charming hotels or guesthouses (double occupancy)
- 4 breakfasts, and 4 dinners featuring local cuisine
- Coffee stops, fruits and snacks, powerbars and gels for everyday use.
- Wine tasting
- Daily luggage transfer between accommodations by van
- Living Roads Kit: hiking jersey and water bottle
- Detailed GPS routes
- Welcome briefing and orientation withe the guide
- Access to the Ride with GPS navigation app
- Single room supplement
- Extra nights before or after the tour
- Transfer from/to starting and ending locations
Included
- 1 expert guide
- 4 nights accommodation in charming hotels or guesthouses (double occupancy)
- 4 breakfasts, and 4 dinners featuring local cuisine
- Coffee stops, fruits and snacks, powerbars and gels for everyday use.
- Wine tasting
- Daily luggage transfer between accommodations by van
- Living Roads Kit: hiking jersey and water bottle
- Detailed GPS routes
- Welcome briefing and orientation withe the guide
- Access to the Ride with GPS navigation app
Not included
- Single room supplement
- Extra nights before or after the tour
- Transfer from/to starting and ending locations
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.
Our tours, both Self-Guided and Full Supported, are ideal for solo travelers.If you choose a Self-Guided experience, you’ll enjoy the freedom of independent travel with the reassurance of our reliable remote support whenever you need it.
Prefer a Full Supported tour? You’ll join a welcoming group of like-minded travelers and be accompanied by expert local guides ready to assist you throughout the journey. Whether you’re riding, hiking, or sharing a meal, you’ll always find connection and shared moments.Traveling solo doesn’t mean being alone, it means choosing your own pace while being part of something meaningful.
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.