Chianti Classico Experience
Duration: 7 days
Trails: T2 trails
Distance: 10 - 15 km / 6 - 9 mi per day
Ascent per day: 250 - 500 m / 820 - 1640 ft ascent per day
> Discover the iconic Chianti wines in their homeland
> Walk from village to village through rolling Tuscan hills
> Enjoy the good life with local specialties and charming accommodations
Experience Chianti the way it was meant to be—at a relaxed pace, walking through vineyards, olive groves, and picturesque Tuscan villages. This journey takes you from the charming town of Greve in Chianti to hidden gems like Panzano, Castellina, and Radda. Along the way, savor the rich flavors of Chianti wines and traditional Tuscan cuisine while soaking in the culture and stunning landscapes. With the perfect balance of activity and relaxation, this is an adventure designed to be enjoyed at your own pace.
The Chianti region is known for its idyllic scenery and centuries-old wine traditions. Walk along rolling hills, quiet country lanes, and cypress-lined paths, with breathtaking views around every corner. Each day brings new discoveries—from historic wine cellars where Chianti wines have aged for generations to charming villages seemingly untouched by time. After a day of walking, unwind in accommodations that reflect the essence of Chianti, from cozy inns to boutique hotels with warm Tuscan hospitality. Picture yourself ending each evening with a glass of Chianti, overlooking the vineyards and hills—an Italian dream come true.
Itinerary
Day
1
Arrival in Greve
Welcome to Greve in Chianti, the heart of the Chianti region and the starting point for your week-long adventure. The town’s historic Piazza Matteotti is lined with charming cafés and wine shops, offering the perfect introduction to Tuscan culture. Settle in with a glass of Chianti Classico, take in the relaxed village atmosphere, and enjoy a gentle start to your journey as you prepare for the beautiful walks ahead.
Albergo Casa Al Sole
Day
2
Greve – Panzano
Duration: 03:20 h
Distance: 11 km / 6.8 mi
Ascent: 480 m / 1575 ft
Descent: 250 m / 820 ft
Today, your adventure through Chianti truly begins as you follow a scenic trail through rolling hills, olive groves, and vineyards. The path includes gentle ascents but remains comfortable and enjoyable. Along the way, take in breathtaking valley views, wander down quiet country lanes, and pass rustic farmhouses that define the Tuscan landscape.
Your destination, Panzano in Chianti, is known for its rich wine culture and the famous butcher Dario Cecchini, where you can taste traditional Tuscan specialties. This picturesque village offers charming restaurants and sunlit terraces, making it the perfect place for a well-deserved break before continuing your journey.
Damario Panorama
Day
3
Panzano – Castellina
Duration: 03:50 h
Distance: 12.9 km / 8 mi
Ascent: 440 m / 1444 ft
Descent: 330 m / 1083 ft
Today's walk takes you along picturesque trails and quiet country roads, winding through the heart of the Chianti wine region. As you walk, enjoy varied landscapes of endless vineyards, rolling hills, and sweeping vistas. Along the way, you’ll pass iconic vineyards where Chianti Classico wines are produced, offering a true taste of Tuscany’s heritage. Your journey leads to Castellina in Chianti, a charming medieval village with narrow stone streets and the impressive Rocca di Castellina fortress. Take a moment to visit a local wine cellar, where you can sample the rich, deep flavors of Chianti wines. End your day by admiring the breathtaking views from the fortress walls, a perfect reward after a day of gentle exploration.
Hotel Colle Etrusco Salivolpi
Day
4
Castellina – Radda
Duration: 04:45 h
Distance: 15.5 km / 9.6 mi
Ascent: 500 m / 1640 ft
Descent: 550 m / 1804 ft
Today’s route follows gentle trails through the rolling Chianti hills toward Radda, making for a relaxed and enjoyable walk with only mild ascents and descents. Along the way, stroll through cypress-lined lanes, sunlit vineyards, and shaded woodlands, soaking in the beauty of the Tuscan countryside at a leisurely pace.
Your journey ends in Radda in Chianti, a picturesque village with cobbled streets, cozy cafés, and inviting terraces. Take the time to unwind and savor a glass of local Chianti wine at one of the charming wine bars, all while enjoying the stunning views of the surrounding hills—the perfect way to end a peaceful day of walking.
Palazzo Leopoldo Dimora Storica & Spa
Day
5
Radda – Gaiole in Chianti
Duration: 04:00 h
Distance: 13.2 km / 8.2 mi
Ascent: 390 m / 1280 ft
Descent: 560 m / 1837 ft
Today's stage is longer and more varied, with a mix of forest paths and open fields, offering both shaded trails and panoramic views of the Chianti hills. As you walk, you’ll pass quiet valleys and peaceful woodland paths, allowing you to fully immerse yourself in the tranquil beauty of Tuscany.
Your destination, Gaiole in Chianti, is famous as the starting point of the historic Eroica bike race and a beloved spot for wine and culture lovers. Take time to visit one of the historic castles, such as the renowned Castello di Brolio, where you can explore its fascinating history and enjoy a tasting of exquisite Chianti wines—a well-earned reward after a fulfilling day of walking.
Casa Vacanze Vertine
Day
6
Gaiole in Chianti – La Madonna
Duration: 04:00 h
Distance: 12 km / 7.5 mi
Ascent: 300 m / 984 ft
Descent: 250 m / 820 ft
On this final day of hiking, you’ll leave Gaiole and make your way to the majestic Castello di Brolio, perched atop a hill and surrounded by rolling vineyards. Here, take a guided tour and enjoy a tasting of Chianti wines, immersing yourself in the rich history of the region.
From the castle, continue your scenic walk through the tranquil Tuscan landscape to La Madonna, where you’ll spend a relaxing evening in the heart of nature. This is the perfect ending to your Chianti journey—a chance to unwind, take in the peaceful surroundings, and enjoy the starry sky as you reflect on a week of discovery and unforgettable moments.
RICASOLI Brolio Agriroom
Day
7
Departure
After one last breakfast surrounded by the beautiful Tuscan landscape, it’s time to say goodbye to the Chianti region. You’ll return home with memories of charming villages, rolling vineyards, and the rich flavors of Chianti wines—perhaps even with a bottle or two to savor later and relive the journey.
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Charisa Kailey-Lê
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