Option 1: 8 km and 350 m of elevation gain / 220 m of elevation loss













Chianti Trail Tuscany Walking Tour
8 days / 7 nights
|
Starting point
Florence
Finish point
Siena
Season
From April to November
Technical level
2/5
Fitness level
2/5
Tour type
Travel & Hike


Starting point
Florence
Finish point
Siena
Season
From April to November
Technical level
2/5
Fitness level
2/5
Tour type
Travel & Hike
- 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 of the trip
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What’s included in the price?
Self-guided
NOT INCLUDED
OPTIONAL EXTRAS
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
Ratings & Reviews

5.0 average rating






We had an incredible time on the 5 day hut to hut hike in Croatia. The views were perfect, the accommodation much nicer than we imagined and we had a fantastic support guide - Ivan - who was very friendly and made the whole trip possible. We were also able to go to the beach most days after we finished our hiking and everything was very flexible. I would highly recommend this to anyone.


1) Stunningly beautiful places with perfect weather! Good balance of countryside and old city walking. 2) The Trip App was incredible!!! 5 stars! Loved the write ups on each location. The links to all restaurants, hotels, attractions, tickets! The GPS app also worked. 3) PERFECTLY located hotels and rooms with two beds and thoughtful staff! Loved being right in the old towns with amazing views. I did not mind carrying bags up or down in order to have the locations but much appreciated when we did have help with this 4) Breakfast being included with the rooms (even though there was a mix up the first morning). I don't like to have to plan breakfast spots and the buffets were incredible. 5) The kindness and promptness of the drivers, Nice transport vehicles and easy drop off and pick up points. Plus help with our bags. 6) The Walking Holidays Croatia team was helpful and easy to work with. We appreciate all they did to customize out trip.


Tour was very well organised with lots of information to help guide us through the holiday. All the accommodation was great. Particularly liked the self catering Glamping Mountain Fairytale and the Berghi Hotel. Food at the Hotel Starkl restaurant was great as well. The route took us through a beautiful part of the country on quiet roads and cycle paths. The cycle paths are much better than in the UK and I would also like to say that Slovenian car drivers are much more patient and tolerant than many drivers in the UK. Beautiful country. Really enjoyed it.
Walking the GR10 was an incredible way to experience the Pyrenees. Each day brought something different—lush valleys, high mountain passes, and charming villages. The huts provided a warm bed, great meals, and a chance to meet fellow hikers. The clear itinerary and support from Hut to Hut Hiking Europe made it easy to focus on enjoying the trail. I’d recommend this hike to anyone looking for a multi-day trek with lots of variety.
My walking holiday in Chamonix and the French Alps was unforgettable. Each day brought stunning views of towering peaks, alpine meadows, and glacial streams. The routes were well-marked and varied in difficulty, making it easy to tailor the days to my pace. The accommodations were charming and perfectly situated for breathtaking morning views. Lan was so helpful in suggesting how to make the most of my time in the region, and their support made the whole trip seamless. If you love mountains and fresh air, this trip is a must!
My walking holiday in Chamonix and the French Alps was unforgettable. Each day brought stunning views of towering peaks, alpine meadows, and glacial streams. The routes were well-marked and varied in difficulty, making it easy to tailor the days to my pace. The accommodations were charming and perfectly situated for breathtaking morning views. Lan was so helpful in suggesting how to make the most of my time in the region, and their support made the whole trip seamless. If you love mountains and fresh air, this trip is a must!
We had an incredible time on the 5 day hut to hut hike in Croatia. The views were perfect, the accommodation much nicer than we imagined and we had a fantastic support guide - Ivan - who was very friendly and made the whole trip possible. We were also able to go to the beach most days after we finished our hiking and everything was very flexible. I would highly recommend this to anyone.


Tour was very well organised with lots of information to help guide us through the holiday. All the accommodation was great. Particularly liked the self catering Glamping Mountain Fairytale and the Berghi Hotel. Food at the Hotel Starkl restaurant was great as well. The route took us through a beautiful part of the country on quiet roads and cycle paths. The cycle paths are much better than in the UK and I would also like to say that Slovenian car drivers are much more patient and tolerant than many drivers in the UK. Beautiful country. Really enjoyed it.
My walking holiday in Chamonix and the French Alps was unforgettable. Each day brought stunning views of towering peaks, alpine meadows, and glacial streams. The routes were well-marked and varied in difficulty, making it easy to tailor the days to my pace. The accommodations were charming and perfectly situated for breathtaking morning views. Lan was so helpful in suggesting how to make the most of my time in the region, and their support made the whole trip seamless. If you love mountains and fresh air, this trip is a must!
1) Stunningly beautiful places with perfect weather! Good balance of countryside and old city walking. 2) The Trip App was incredible!!! 5 stars! Loved the write ups on each location. The links to all restaurants, hotels, attractions, tickets! The GPS app also worked. 3) PERFECTLY located hotels and rooms with two beds and thoughtful staff! Loved being right in the old towns with amazing views. I did not mind carrying bags up or down in order to have the locations but much appreciated when we did have help with this 4) Breakfast being included with the rooms (even though there was a mix up the first morning). I don't like to have to plan breakfast spots and the buffets were incredible. 5) The kindness and promptness of the drivers, Nice transport vehicles and easy drop off and pick up points. Plus help with our bags. 6) The Walking Holidays Croatia team was helpful and easy to work with. We appreciate all they did to customize out trip.


Walking the GR10 was an incredible way to experience the Pyrenees. Each day brought something different—lush valleys, high mountain passes, and charming villages. The huts provided a warm bed, great meals, and a chance to meet fellow hikers. The clear itinerary and support from Hut to Hut Hiking Europe made it easy to focus on enjoying the trail. I’d recommend this hike to anyone looking for a multi-day trek with lots of variety.
My walking holiday in Chamonix and the French Alps was unforgettable. Each day brought stunning views of towering peaks, alpine meadows, and glacial streams. The routes were well-marked and varied in difficulty, making it easy to tailor the days to my pace. The accommodations were charming and perfectly situated for breathtaking morning views. Lan was so helpful in suggesting how to make the most of my time in the region, and their support made the whole trip seamless. If you love mountains and fresh air, this trip is a must!
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