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






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.


We give Hut-to-Hut our highest recommendation! They organized a fantastic and perfectly challenging hike for us in the beautiful Brenta Dolomites in Italy. From start to finish, communication with the agency was smooth, quick, and helpful. Any questions or special requests we had were handled promptly. We hiked independently using the GPS app they provided, which was super easy to use and made navigation stress-free. Each night, we stayed in charming refugios or hotels - complete with three delicious meals, refreshing little lakes to swim in, and plenty of peaceful spots to recharge before the next day’s adventure. A memorable and well-organized experience!
My husband and I recently completed a Walking Holiday of the Amalfi Coast for 11 days, which was absolutely fantastic and the highlight of our trip to Italy. The travel agents who organised the tour Anja and Samo were very helpful, adjusting and customising it to suit our requests. The accomodation booked for us was very comfortable and the transfer of our luggage from hotel to hotel took place with no issues. Our hiking guides including Alessandra, Marcella and Diego were all exceptional. They were friendly, supportive and extremely knowledgable about the towns and regions we walked in. They ensured we had a fantastic experience creating memories, while enjoying the walking, the amazing views, the tasty food and the beautiful Italian culture. I highly recommend this walking tour and would encourage anyone who was planning a similar holiday to book through this company. It was a great way to see and experience the Amalfi Coast.
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 husband and I recently completed a Walking Holiday of the Amalfi Coast for 11 days, which was absolutely fantastic and the highlight of our trip to Italy. The travel agents who organised the tour Anja and Samo were very helpful, adjusting and customising it to suit our requests. The accomodation booked for us was very comfortable and the transfer of our luggage from hotel to hotel took place with no issues. Our hiking guides including Alessandra, Marcella and Diego were all exceptional. They were friendly, supportive and extremely knowledgable about the towns and regions we walked in. They ensured we had a fantastic experience creating memories, while enjoying the walking, the amazing views, the tasty food and the beautiful Italian culture. I highly recommend this walking tour and would encourage anyone who was planning a similar holiday to book through this company. It was a great way to see and experience the Amalfi Coast.
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.


We give Hut-to-Hut our highest recommendation! They organized a fantastic and perfectly challenging hike for us in the beautiful Brenta Dolomites in Italy. From start to finish, communication with the agency was smooth, quick, and helpful. Any questions or special requests we had were handled promptly. We hiked independently using the GPS app they provided, which was super easy to use and made navigation stress-free. Each night, we stayed in charming refugios or hotels - complete with three delicious meals, refreshing little lakes to swim in, and plenty of peaceful spots to recharge before the next day’s adventure. A memorable and well-organized experience!
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.
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