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Chianti Trail Tuscany Walking Holidays

Embark on a walking adventure through Tuscany's Chianti region, renowned for its artistry, fine architecture, delectable wine, and stunning landscapes.
Starting point
Finish point
8 days / 7 nights
Tour type
From: 789€/person

Explore the stunning landscapes of Tuscany and Chianti on foot

Immerse yourself in the Renaissance history of Siena and Florence

Sample the exquisite wines of Chianti

Walk through rolling hills and take in the stunning views of medieval towns below

Culinary delights in siena

Taste the flavors of Tuscany in historic Siena with us


Wind through vineyards for world-renowned wines

Florence and arno river

Admire Florence on foot, an iconic part of your tour

Finest chianti wine

Savor Chianti's wines, your glass awaits

Medieval siena

Take in Siena's grandeur

Included in price

Tour design and organization

24/7 service and support during your holidays

GPS navigation with an easy-to-use app

7-night accommodation with breakfast in 3* hotels

Luggage transfer

Transfers per itinerary


Tuscany’s rolling hills, vineyards, and historic cities await you on an immersive walking journey that will feed your artistic soul and let you explore the magical landscape on foot.

The holiday will take you to Tuscany’s most iconic landmarks, such as the medieval towns of Florence and Siena, and to quaint villages like Panzano. Along the way, you’ll discover ancient Roman farmsteads hidden amongst the hills, adding a touch of history and intrigue to your walk.

Our walking holiday has a carefully planned itinerary that showcases the highlights of the Chianti region without feeling rushed or overwhelmed. You’ll 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 daily excursions punctuated by visits to historical landmarks like 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 detailed itinerary booklet to guide you. We offer 24/7 support and coordinate transfers to ensure a hassle-free experience.

Join our walking holiday on the Chianti Trail in Tuscany and experience a little piece of heaven on Earth that you can take back home with you.


For travellers that want flexibility and independence. We organize the tours of your choice, but the adventure of getting around is all yours. You will get a fly & drive itinerary handout with activities, accommodations and travelling tips with full support of our team for any emergencies or concerns. You will take yourself around Slovenia, but we can arrange a car rental or even a campervan if you wish.

Handpicked Adventures

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


We book the activities, accommodations, transfers and anything else you prefer not to deal with, so you can enjoy a carefree adventure.

Trusted by Many

We are a fully bonded and insured travel company, keeping your money safe and with thousands of satisfied customers in the past, we still put you first.

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.

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