Explore the stunning landscapes of Tuscany and Chianti on foot
Immerse yourself in the Renaissance history of Siena and Florence
Sample the exquisite wines of Chianti
Walk through rolling hills and take in the stunning views of medieval towns below
Upon arrival in Florence, your Chianti walking tour commences, immersing you in the city’s Renaissance charm, picturesque piazzas, and stunning architecture. Take a leisurely stroll along the banks of the Arno River, taking in the city’s iconic landmarks and rich history.
Make your way to the historic Piazza della Signoria, home to one of Florence’s most famous squares. Here, you can marvel at the impressive statues and stunning architecture while enjoying the lively atmosphere of the bustling square. As the evening approaches, indulge in culinary delights at one of the many outstanding restaurants in the area, offering an array of delicious Tuscan cuisine.
Overnight in Florence
Commence your day with a delectable breakfast and take a 25-minute local bus ride into the peaceful hills of Tuscany. Set off from Settignano for a picturesque walk through the stunning countryside, choose from two different trails that offer magnificent views of Florence, with grand Renaissance villas, fragrant cypress trees, and lush olive groves. Later, explore the historic 7th-century town of Fiesole and discover fascinating Etruscan ruins, a Roman amphitheater, and a peaceful Franciscan monastery.
Overnight in Fiesole
Option A: 8 km, 350 meters of elevation gain, and 220 meters of elevation loss (3 hours of walking time)
Option B: 16 km and 570 meters of elevation gain/loss (6 hours of walking time)
Start your day with a quick transfer to the charming town of Greve in Chianti, where you’ll find some of the finest wine in the region. Once you’ve checked into your hotel, head over to Le Cantine di Greve for a tasting of over 50 varieties of local wine.
Then, you’ll have two choices for today’s walk:
The first route begins in Greve’s main square and takes you through the scenic Chianti Classico region, offering breathtaking views of the sprawling vineyards and the “azende agricole” farms where they produce the iconic Chianti wine.
The second route leads you through the lush, wild vegetation of the nearby forest, with olive groves and vineyards lining the way. Along the trail, you’ll come across abandoned farms and stunning villas, with the occasional stop to admire the panoramic view from Montefioralle.
Overnight in Greve
Option A: 11.5 km and 430 meters of elevation gain/loss (4 hours of walking time)
Option B: 10 km and 350 meters of elevation gain/loss (3.5 hours of walking time)
Embark on a scenic looped walk that begins in the picturesque village of Panzano on this day’s adventure. Take a stroll through the charming medieval streets of this historic town before heading out to explore the rolling hills of the classic Chianti trail, which offers a stunning mix of natural beauty, with forests and vineyards alternating along the way. As you walk, you’ll encounter ancient Roman farmsteads, adding a touch of history and intrigue to your journey.
Overnight in Panzano
400 meters of elevation gain/loss
4 hours of walking time
Begin your day with a delightful breakfast, followed by a brief car ride to Monte San Michele, the highest point in the Chianti hills. As you walk through a picturesque valley flanked by magnificent hundred-year-old chestnut trees, you’ll make your way to the charming medieval hamlet of Volpaia, surrounded by vineyards and castles.
Take a break at one of the area’s best wine shops or “enotecas” to sample a glass of red wine before heading to the quaint medieval walled town of Radda in Chianti.
Overnight in Radda
Begin your day by exploring the enchanting old town center of Radda, taking in the beauty of the historic landmarks. Stroll through the winding alleyways that lead to the magnificent church of Santa Maria Novella.
As you make your way through the picturesque vineyards, stop at one of the local wineries to indulge in the renowned wines of the region. Don’t forget to pause and admire the stunning views along the way.
600 meters of elevation gain/loss
5 hours of walking time
On your final full day, move to Siena to savor the flavors of the city on a guided food tour. Your knowledgeable guide will lead you on a delightful walk through this Gothic and medieval city, showcasing its UNESCO World Heritage sites, including the oldest bank in the world and the stunning Piazza del Campo. During the tour, you’ll indulge in local food and Chianti wine, with specialties such as the Pecorino cheese, Salame Toscano, Finocchiona, handmade bread, prosciutto, and Siena’s famous Ricciarelli sweets.
Overnight in Siena
Regrettably, your stay with us in Tuscany comes to an end after breakfast. However, if your flight isn’t immediate, you are free to spend the rest of the day exploring more of Siena at your leisure.
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Tour design and organization
24/7 service and support during your holidays
GPS navigation with an easy-to-use app
7-night accommodation with breakfast in 3* hotels
Transfers per itinerary
Tuscany’s rolling hills, vineyards, and historic cities await you on an immersive walking journey that will feed your artistic soul and let you explore the magical landscape on foot.
The holiday will take you to Tuscany’s most iconic landmarks, such as the medieval towns of Florence and Siena, and to quaint villages like Panzano. Along the way, you’ll discover ancient Roman farmsteads hidden amongst the hills, adding a touch of history and intrigue to your walk.
Our walking holiday has a carefully planned itinerary that showcases the highlights of the Chianti region without feeling rushed or overwhelmed. You’ll enjoy a relaxing, well-paced walk each day, with ample time to explore each location and take in the scenery.
You’ll have the opportunity to taste some of the world-renowned wines of the Chianti region, stopping at local wineries for a glass or two. The walking routes wind through forests and vineyards, offering breathtaking vistas, with daily excursions punctuated by visits to historical landmarks like the church of Santa Maria Novella.
And the best thing of all? Our team takes care of every detail, from booking accommodations to providing GPS tracks for each route and a detailed itinerary booklet to guide you. We offer 24/7 support and coordinate transfers to ensure a hassle-free experience.
Join our walking holiday on the Chianti Trail in Tuscany and experience a little piece of heaven on Earth that you can take back home with you.
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