Chianti Trail Tuscany Walking Tour
Experience the breathtaking landscapes of Tuscany and Chianti on foot
Immerse yourself in the rich Renaissance history of Siena and Florence
Indulge in the exquisite local wines of Chianti
Walk across rolling hills, enjoying stunning views of the medieval towns below
Take advantage of our expertly planned itinerary and GPS tracks to maximize your adventure
Itinerary
As you arrive in Florence, the adventure of your Chianti walking tour begins. Immerse yourself in the city’s atmosphere, exploring its splendid Renaissance architecture and picturesque squares. Take a leisurely walk along the banks of the Arno River, soaking in the beauty of the city’s iconic landmarks.
Make your way towards the Piazza della Signoria, one of Florence’s most famous and historic squares. As the evening approaches, treat yourself to culinary delight at one of the many outstanding restaurants in the area, offering an array of delicious Tuscan cuisine.
Start your day off with a delicious breakfast before embarking on a 25-minute local bus ride up into the serene hills of Tuscany. You’ll begin today’s walk in Settignano. You can choose from two different trails. Both offer a picturesque walk through the stunning Tuscan countryside, with fragrant cypress trees, lush olive groves, grand Renaissance villas, and views of Florence.
Afterward, stroll through the quaint and historic 7th-century town of Fiesole, where you can explore fascinating Etruscan ruins, a Roman amphitheater, and a peaceful Franciscan monastery.
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)
Begin 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.
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)
Today’s adventure begins with a beautiful looped walk starting in the enchanting village of Panzano. Take a moment to explore the charming medieval streets of this historic town before embarking on your journey through the rolling hills.
The classic Chianti trail offers a delightful blend of natural beauty, alternating between forests and vineyards, providing plenty of opportunities to take in the stunning scenery of Tuscany. Along the way, you will see ancient Roman farmsteads, adding a touch of history and intrigue to your walk.
12 km
400 meters of elevation gain/loss
4 hours of walking time
Start your day with a delicious breakfast before a short car transfer takes you to the breathtaking Monte San Michele, the highest point of the Chianti hills. From there, you’ll descend through a scenic valley surrounded by majestic century-old chestnut trees and continue toward the picturesque medieval hamlet of Volpaia, nestled among vineyards and castles.
Stop at one of the region’s finest wine shops, or “enotecas,” to enjoy a glass of red wine before continuing your journey towards the charming medieval walled town of Radda in Chianti.
Begin today’s journey with a tour of the charming old center of Radda, taking in the sights and sounds of this historic town. Then, follow the winding alleyways as they lead you toward the stunning church of Santa Maria Novella.
As you walk through the picturesque vineyards, don’t hesitate to stop at one of the excellent local wineries for a taste of the region’s renowned wines. The views from this walk are sure to take your breath away.
16 km
600 meters of elevation gain/loss
5 hours of walking time
Today is free for you to enjoy Siena at your own pace and explore its many charms at your leisure. Start your day with a delicious breakfast before transferring to the stunning city of Siena. This city is a treasure trove of Renaissance history and architectural wonders.
Admire the shell-shaped square where the thrilling Palio horse race is held biannually, and explore the impressive Duomo, a marvel of Gothic architecture. Wander through the winding streets and admire the medieval palaces and towers that dot the city’s skyline.
Sadly, nothing lasts forever, and your time with us in Tuscany runs out after breakfast. If you are not in a rush with your flight, you are welcome to explore the city for as long as you wish.
Pricing
Included in price
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
Luggage transfer
Transfers per itinerary
Description
Here is your chance to embark on an immersive journey past Tuscany’s rolling hills, vineyards, and historic cities, feeding your artistic soul in the land of Michelangelo while exploring the magical landscape on foot.
Walking holidays in Tuscany is the perfect way to see the region’s most iconic landmarks, such as the medieval towns of Florence and Siena. In addition, you will visit quaint villages, such as Panzano, and discover ancient Roman farmsteads hidden amongst the hills.
This walking tour has a carefully planned itinerary that showcases the highlights of the Chianti region without feeling rushed or overwhelmed. You will 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 your daily excursions punctuated by visits to historical landmarks, such as 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 written booklet to guide you. We offer 24/7 support and coordinate transfers to ensure a hassle-free experience.
Join our walking tour in Tuscany and grab a little piece of heaven on Earth to take back home with you.
Location
Things to know
Our tours are designed to cater to a broad range of people, but some days can be quite challenging, with long distances and significant elevation gain. We aim to minimize this as much as possible while ensuring a high-quality experience. To fully enjoy our tours, you should be accustomed to walking for 4-6 hours, overcoming around 600 meters of elevation gain.
However, Alta Via 1 hut-to-hut hikes and Tour du Mont Blanc are more demanding and require a higher fitness level. On these tours, you may need to hike up to 8 hours per day and tackle substantial elevation gain.
Yes, our hiking holidays are appropriate for children who are physically prepared and have a good balance. However, to guarantee the safety and enjoyment of our young participants, we suggest that they should be at least eight years old to join our tours.
Proper footwear is crucial for our walking tours. We recommend wearing sturdy hiking shoes with ankle support for all our hikes. The terrain can be uneven, rocky, and slippery. Wearing sneakers can be dangerous, especially if you are not accustomed to hiking on such surfaces, as they do not offer enough protection and support. Robust shoes also provide the necessary support when your legs get tired during long hikes.
Yes, we highly recommend booking in advance to secure your spot. The earlier you book, the better the chances are of getting your preferred options. If you book close to the start of the season or during the season, we may not be able to guarantee availability in the hotels and apartments. Therefore, it is best to make reservations as soon as possible to avoid any inconvenience.
It is essential to note that accommodations at the destinations of our walking tours are in high demand during the summer season. Therefore, early booking is crucial to secure your preferred type of housing. However, we assure you that we will always try our best to provide you with the most suitable lodging based on your preferences. Rest assured that we will do everything possible to ensure that your stay is comfortable and enjoyable.
Our tours are well-organized, and all the destinations are easily accessible and straightforward to navigate. Therefore, it is unlikely that you will require a guide. Our comprehensive handout will provide you with all the essential information while still allowing you the freedom of a self-guided holiday.
However, if you prefer to have a guide, please let us know, and we will make the necessary arrangements for you.
Most of the accommodations we provide offer vegetarian and vegan options for breakfast. Additionally, you will find no shortage of vegetarian and vegan menus in restaurants during the tour. However, it is worth noting that some mountain huts on Alta Via 1 or Tour du Mont Blanc may not offer vegan meals. In such situations, it is advisable to bring your own food to ensure that your dietary needs are met.
The best time to go on a walking holiday in Italy varies depending on the location you plan to visit. Destinations such as the Amalfi Coast, Cinque Terre, and Sicily are best visited during early spring and fall when the weather is pleasant, and the crowds are fewer.
However, in areas like the Dolomites or around Mont Blanc, hiking is not possible when there is snow high up in the mountains. Therefore, the hiking season in these areas is limited from late June to late September. It is advisable to plan your trip accordingly to get the best out of your walking holiday in Italy.
We can best advise you after receiving a filled-out inquiry form.
While hiking in light rain is manageable, it is important to note that hiking during a storm can be dangerous. It is advisable to schedule hikes early in the day during the summer months to avoid thunderstorms. However, if the weather forecast predicts severe weather, it is best to reschedule your walk for another day or explore different tour options.
Your safety is our top priority, and we will always work with you to find a suitable solution in case of inclement weather.
Most of the destinations for our walking tours in Italy have excellent public transportation. While renting a car can provide flexibility, several locations cannot be comfortably accessed by car. Instead, we suggest relying on public transport to reduce stress and have a more environmentally friendly experience.
We provide all the necessary information for buses, trains, and ferries to ensure that you can reach your destination with ease. By using public transport, we can also reduce our carbon footprint and contribute to a more sustainable travel experience.