Product image 0
Product image 0
Product image 1
Product image 2
Product image 3
Product image 4
Product image 5
Product image 6
Product image 7
Product image 8
1/10

Chianti Trail Tuscany Walking Tour

8 days / 7 nights

|

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

Choose your style

Cancel in the first 48h for free
Reserve your spot with a minimum deposit
Samo Korelec
SamoTravel Expert
Book a call
Google ReviewsTripAdvisor Reviews
  • 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
Transfers

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 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.

Ratings & Reviews

Google Reviews

5.0 average rating

Top Rated Brand

Similar Products

All available guidance options

Join a Group

For solo hikers or hikers who wish to meet other like-minded souls...

Private Guided Group

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

Self-guided

Those who like a good adventure and limitless flexibility should go on a self-guided tour...

Hassle-Free

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

Trusted by Many

We are a financially protected company, fully bonded and insured, keeping your money safe and allowing you to travel with confidence.

Handpicked Adventures

Handpicked Adventures

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

Unbeatable Support

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