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













Chianti Trail Tuscany Walking Tour
8 days / 7 nights
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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
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Starting point
Florence
Finish point
Siena
Season
From April to November
Technical level
2/5
Fitness level
2/5
Tour type
Travel & Hike
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
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
All available guidance options
Join a Group
If you are a solo cyclist who wants to spend a fun holiday cycling, look no further...
Private Guided Solo
The private guided bike tour is for those who want to enjoy their cycling holidays at their own pace...
Private Guided Group
The private guided bike tour is for those who want to enjoy their cycling holidays at their own pace...
Self-guided
Those who like a good adventure and limitless flexibility should go on a self-guided cycling holiday...
HANDPICKED ADVENTURES
Only the best adventures across the world, cherry-picked by our team with an in-depth knowledge of the regions.
VALUE YOUR TIME
With everything on your plate, let us handle the vacation planning, so your valuable time stays exactly where you need it.
SELF-GUIDED TRAVEL
Explore independently and with confidence while we keep everything running from behind the scenes.
TRUSTED BY MANY
Since 2014, we have taken care of thousands of happy customers, making it our mission to put your satisfaction first.
OUTDOOR SPECIALISTS
We are a team of outdoor specialists equipped with the knowledge and insight to bring you the best hiking experiences.








































