Winding road lined with cypress trees through rolling green hills at sunset in Tuscany
Woman dining on pizza and orange cocktail overlooking Siena cityscape and Duomo.
Rolling green hills covered in sunlit vineyards and scattered houses in Tuscany, Italy
Florence cityscape with Ponte Vecchio bridge over the Arno River and distant mountains
Man smelling red wine in a sunlit vineyard with green grapevines
Rooftops of medieval Siena with the striped Duomo tower and surrounding Tuscan hills under a blue sky.
Winding road lined with cypress trees through rolling green hills in Tuscany at sunset.
Pasta ingredients including dried pasta, tomatoes, Parmesan, mozzarella, olives, and herbs for Tuscan cuisine.
View of Siena city skyline above rolling green Tuscan hills with cypress trees under a blue sky.
Michelangelo's David marble statue displayed indoors under a domed ceiling
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Chianti Trail Tuscany Walking Tour

8 days / 7 nights

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Stroll the land of artistry, finest architecture, savory wine, and heavenly landscape on this walking tour across the Chianti region of Tuscany.

Starting point

Florence

Finish point

Siena

Season

From April to November

Technical level

2/5

Fitness level

2/5

Tour type

Travel & Hike

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Highlights

  • 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

What’s included in the price?

Self-guided

7 nights in 3-star hotels with breakfast
Digital guidebook with itinerary, route instructions, and practical information
GPS navigation with an easy-to-use app
Tour design and organization
Service and support during your hike

NOT INCLUDED

Tourist tax

OPTIONAL EXTRAS

Hotel upgrades
Luggage transfer
Single supplement

What to bring to the tour

  • Hiking shoes/boots
  • 25 to 35-liter backpack
  • Base layer
  • Sports T-shirts
  • Hiking shorts
  • Hiking water-repellent pants
  • Waterproof jacket
  • Midlayer
  • Sports socks and underwear
  • Leisurewear for evenings
  • Shade hat/cap
  • Sunscreen
  • Sunglasses
  • Hiking poles
  • ID card or passport
  • Snacks
  • Cash
  • Water bottles or hydration pack
  • Toiletries

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 digital guidebook to guide you. We offer round-the-clock 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.

Frequently Asked Questions

Our walking holidays in Tuscany are primarily focused on leisurely exploration, offering a delightful experience without significant elevation gain. However, it’s important to note that certain stages of the Via Francigena can be quite long. In addition, we also offer other holiday options that include more demanding hikes. Regardless of the holiday you choose, we aim to provide a high-quality experience catering to different fitness levels. So, whether you prefer leisurely strolls through the picturesque Tuscan countryside or more demanding hikes to push your limits, we have options to suit your preferences and ensure a fulfilling journey.

Absolutely! Our hiking holidays are designed to be inclusive and can be enjoyed by people of various age groups, including children. Most of our tours do not include technically demanding terrain. We believe in the importance of providing opportunities for children to embrace the outdoors and experience the joys of hiking. While a minimum age of eight is recommended to ensure safety and engagement, our tours are generally suitable for individuals who possess basic physical capabilities and can comfortably walk for a few hours daily.

For our walking tours, we highly recommend wearing sturdier hiking shoes that provide ample support, particularly during long hiking days and on uneven terrain. Hiking shoes are designed specifically for outdoor activities, offering features such as sturdy soles, enhanced traction, and ankle support. They are well-suited to handle various terrains, including gravel paths, rocky trails, and uneven surfaces commonly encountered during our walking tours. Opting for appropriate footwear ensures comfort and stability and minimises the risk of foot fatigue or potential injuries.

We highly recommend making an advance booking to ensure accommodation availability. Securing your reservation early increases the likelihood of obtaining your preferred options. If you wait until the start of the season or during the season, availability in hotels and apartments may be limited, and we may not be able to guarantee your desired arrangements.

It’s important to be aware that accommodations at the destinations are in high demand, especially during the summer season. To secure your preferred type of housing, we strongly recommend booking early. By doing so, you increase the likelihood of obtaining the accommodation that best suits your preferences. While the availability of specific lodging options may vary, we assure you that we will make every effort to provide you with the most suitable accommodations based on your preferences. Our team is dedicated to ensuring your stay is comfortable and enjoyable, and we strive to meet your specific requirements to the best of our ability.

Our tours are meticulously planned and designed to be easily navigated by independent travelers. The destinations are well-marked and accessible, allowing you to explore at your own pace. As such, it is unlikely that you will require a guide during your tour.


To ensure you have all the necessary information and guidance, we provide a comprehensive handout that covers essential details about the routes, points of interest, and practical tips. This enables you to enjoy the freedom and flexibility of a self-guided holiday, where you can fully immerse yourself in the experience and discover the beauty of each destination at your leisure.


However, if you prefer to have a guide accompany you during the tours, we are more than happy to accommodate your request. Simply let us know in advance, and we will make the necessary arrangements to provide you with a knowledgeable guide who can enhance your journey with insightful commentary and assistance.

The best time to go on a walking holiday in Tuscany is during the early spring and fall seasons. During these periods, the weather is pleasant, and the crowds are fewer, allowing for a more tranquil and enjoyable experience.


In the early spring, typically from March to May, you can witness the region come alive with vibrant blossoms and lush greenery. The temperatures are mild, making it perfect for exploring the picturesque landscapes of Tuscany on foot. Additionally, the tourist crowds are relatively smaller during this time, providing you with a more intimate and serene setting to immerse yourself in the beauty of the surroundings.


Similarly, the fall season, from September to November, offers a delightful time to visit. The weather remains pleasant, with comfortable temperatures ideal for walking and exploring. The autumn colours add a captivating charm to the landscapes, creating a picturesque backdrop for your walking tour. With fewer visitors compared to the peak summer months, you can fully appreciate the tranquillity and authenticity of the region.


It’s worth noting that the summer months in Tuscany, particularly July, and August, can be quite hot and crowded. While the region maintains its allure during this time, the higher temperatures and increased tourist influx may impact your overall experience. However, if you plan accordingly and take precautions against the heat and the crowds, summer can still offer enjoyable walking opportunities in Tuscany.

In cases of light rain or mild weather disturbances, hiking can often still be safely managed as long as it does not pose any significant risks. The stunning landscapes of Tuscany can take on a unique charm under a drizzle, offering a different perspective and an enchanting experience.


However, in situations where the weather becomes more severe, such as heavy rainstorms or thunderstorms, our team will assess the situation and make appropriate adjustments to ensure your safety. This may involve modifying the planned routes, seeking shelter, or postponing the activity until the weather improves.

All available guidance options

Private Guided Solo

Experience the great outdoors on a private guided tour tailored just for you...

Private Guided Group

Get together a group of your buddies and leave the rest to us! All you have to do is sit back, relax and enjoy a tour built around your group’s preferences. With an experienced guide accompanying you every step of the way, you’ll get the most out of your hike without having to stress about the details.

Self-guided

Are you looking for a good adventure and limitless flexibility? Then you should try out a self-guided tour, perfect for independent explorers who want to set their own pace. Without the need to stick to a group schedule, you’re free to linger at scenic viewpoints while the logistics are taken care of in advance.

HASSLE-FREE

We handle itineraries, accommodations, and anything else you prefer not to deal with, so you can enjoy a carefree hike.

TRUSTED BY MANY

We are a financially protected company operating since 2014, and with thousands of satisfied customers in the past, we still put you first.

TRIED & TESTED ADVENTURES

Only the best walking tours in Tuscany, cherry-picked by our team with an in-depth knowledge of the region.

UNBEATABLE SUPPORT

Our 24/7 customer support is where we show our passion, bringing you a better experience by making your well-being our number one priority.

from 1.085 € /person
Experience the enchanting mediaeval towns, luscious cuisine, and rolling vineyard landscapes with Tuscany Walking Holidays, your gateway to Italian adventures.

Have questions? Talk to us.

Anja Hajnšek
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