Chianti Trail Tuscany Walking Holidays

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.

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.

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.

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.

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.

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.

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.

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.