Via Sanese Odyssey: Hiking Journey Through Tuscany's Heart
Itinerary
Your Tuscany hiking journey begins in Florence, where Renaissance landmarks mark the start of the ancient Via Sanese. Leaving the city behind, you head into the scenic hills of Chianti. The trail leads through vineyards, forests, and medieval villages, offering panoramic views and a taste of Tuscany’s rural charm. You pass historic towns like San Casciano and Castellina in Chianti, rich in tradition and architectural beauty. Along the way, quiet hamlets, old monasteries, and classic Tuscan landscapes define the peaceful rhythm of the hike. The journey ends in Siena, where Gothic towers and the famous Piazza del Campo offer a stunning finale to your four-day adventure.
Highlights
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Begin your journey in Florence, surrounded by iconic Renaissance landmarks
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Hike through the scenic hills and vineyards of Chianti
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Explore charming medieval villages like San Casciano and Castellina
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Wander past quiet hamlets, historic monasteries, and classic Tuscan landscapes
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Enjoy panoramic views and the peaceful rhythm of rural Tuscany
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Conclude in Siena with its breathtaking towers and the famous Piazza del Campo
Day 1 - Florence to San Casciano Val di Pesa
Your Tuscany hiking adventure begins in Florence, surrounded by Renaissance landmarks like the Cathedral of Santa Maria del Fiore and the Baptistery of San Giovanni. Crossing the famous Ponte Vecchio, you leave the city behind and follow the historic Via Sanese trail into the hills, passing the Certosa monastery near Galluzzo. The route takes you through Tavarnuzze and along scenic ridgelines with sweeping countryside views before descending into a quiet valley. You reach San Casciano Val di Pesa, a well-preserved medieval town that once served as a key fortress between Florence and Siena.
Level 4 - Challenging
22Km
Activity
HikingDay 2 - San Casciano to Badia a Passignano
Your second day begins in San Casciano Val di Pesa, as you hike into the heart of the Chianti Classico wine region, surrounded by rolling vineyards. Climbing through historic wine estates, you enjoy sweeping views of the Pesa Valley and pass through landscapes shaped by centuries of winemaking. The trail continues through wooded hills to the medieval hamlet of Montefiridolfi and the quiet forest settlement of Valigondoli. Your day ends at Badia a Passignano, a grand 10th-century abbey nestled among ancient vineyards, rich in history and beauty.
Level 3 - Moderate
15Km
Activity
Hiking
Day 3 - Badia a Passignano to Castellina in Chianti
Your third day begins at Badia a Passignano, with stunning views of the abbey and surrounding vineyards as you follow a scenic white gravel road. The trail leads to the peaceful sanctuary of Madonna di Pietracupa, set among olive groves and cypress trees in the Chianti hills. You then hike through dense, ancient forests filled with wildlife, following quiet, shady paths that reflect the region’s natural beauty. The day ends in Castellina in Chianti, a historic hilltop fortress town with medieval walls and towers, offering sweeping views of the Chianti landscape.
Level 4 - Challenging
21Km
Activity
HikingDay 4 - Castellina in Chianti to Siena
Your final day begins in Castellina in Chianti, following ancient forest trails toward the historic Fonterutoli wine estate. At Fonterutoli, centuries of Chianti Classico winemaking tradition come to life amid Renaissance villas and ancient cellars. The trail winds through vineyards, olive groves, and quiet villages like Quercegrossa and Basciano, showcasing timeless Tuscan rural life. Your journey concludes as Siena’s iconic skyline comes into view, marking a grand finale to your four-day hike through Tuscany.
Level 5 - Very challenging
25Km
Activity
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Day 5- A Toast to the Journey
With Siena’s towers still fresh in your memory, the final day is reserved for farewells and reflection. It’s a chance to relive the trails, towns, and timeless landscapes that shaped your Tuscan adventure, while letting anticipation grow for the next path yet to be discovered.
Level 1 - Very easy
Activity
Relax & DiscoverFrom Florence’s Heart to the Hills
Your journey begins in Florence’s majestic historic center, where Renaissance landmarks like the Cathedral of Santa Maria del Fiore set the stage. As you cross the iconic Ponte Vecchio, lined with medieval goldsmith shops, you leave the city's energy behind and step into the timeless beauty of the Tuscan hills. It’s a moment that marks the transition from urban splendor to countryside serenity.
Walking Through Centuries of Wine Tradition
As you enter the Chianti region, the trail winds through rolling hills covered in rows of Sangiovese vines that have shaped the landscape for over 700 years. Passing historic wine estates and olive groves, you don’t just see Tuscany, you taste its legacy. This stretch is a dream for wine lovers and scenery seekers alike.
Soulful Silence at Badia a Passignano
Approaching the 10th-century Badia a Passignano abbey on a quiet white gravel road, you're treated to one of the most serene and visually striking moments of the trek. Surrounded by ancient vineyards and timeless countryside, the abbey embodies Tuscany’s deep blend of faith, history, and natural beauty.
A Grand Arrival in Siena
After days of forests, vineyards, and hilltop villages, your journey ends as Siena’s Gothic towers rise on the horizon. Entering this historic city, with its fan-shaped Piazza del Campo and striking Duomo, delivers a cinematic conclusion—both awe-inspiring and deeply rewarding. It’s the perfect final note to your Via Sanese adventure.
Important info
- 1 expert guide
- 4 nights accommodation in charming hotels or guesthouses (double occupancy)
- 4 breakfasts, and 4 dinners featuring local cuisine
- Coffeè stops, fruits and snacks, powerbar and gels for everyday use.
- Wine tasting
- Daily luggage transfer between accommodations with the 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
- Coffeè stops, fruits and snacks, powerbar and gels for everyday use.
- Wine tasting
- Daily luggage transfer between accommodations with the 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.
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.
In most cases, yes. Transfer details will be clearly stated when you book your trip. If included, a representative will meet you at the airport/train station upon arrival.
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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.