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Chianti Walking Holidays

Embark on a journey through the Chianti region, a land renowned for its artistic heritage, architectural marvels, delectable wines, and unique landscapes.
Starting point
Finish point
8 days / 7 nights
Apr - Nov
From: 945€/person
Leisurely to Moderate
Suitable for most people with basic stamina and walking experience

Traverse the awe-inspiring terrains of Tuscany and Chianti on foot

Delve into the abundant Renaissance heritage of Siena and Florence

Savour the exceptional local wines of the Chianti region

Trek through undulating hills, taking in the spectacular vistas of the ancient towns beneath

Leverage our meticulously designed itinerary and GPS routes to enhance your exploration

female hiker walking across tuscany hills
Hike through Tuscany's undulating hills
A man sipping a glass of Chianti wine with breathtaking views of Tuscany - Italian region famous for its picturesque landscapes and excellent wines -  ai generative
Savor world-famous Chianti wine with a breathtaking view
Chianti hills with vineyards and cypress. Tuscan Landscape between Siena and Florence. Italy
Explore enchanting landscapes and ancient Roman homesteads
Culinary delights in siena
Indulge in a leisurely feast amidst the charm of Siena
Woman is walking in a tuscan countryside
Immerse in Chianti's awe-inspiring beauty, one step at a time
Sunset view of Florence and Duomo. Italy
Witness the captivating sunset panorama over Florence
Siena city skyline, countryside and rolling hills. Tuscany, Italy
Soak in the timeless skyline of Siena, a medieval marvel
Uffizi Gallery. Piazza degli Uffizi square in the early Sunny autumn morning. Florence, Tuscany, Italy
Nourish your artistic spirit in the land of Michelangelo

Included in price

Tour design and organisation

24/7 service and support during your holidays

GPS navigation with an easy-to-use app

7x accommodation with breakfast in 3* hotels

Luggage transfer

Transfers as per itinerary

Optional Extras

Transfer to and from the airport
Single supplement

Seize this opportunity to embark on a captivating journey through Tuscany’s undulating hills, vineyards, and historic cities, nourishing your artistic spirit in the land of Michelangelo while exploring the enchanting landscape on foot.

The Chianti trail is the ideal way to experience the region’s most iconic landmarks, such as the medieval cities of Florence and Siena. Additionally, you’ll visit charming hamlets like Panzano and uncover ancient Roman homesteads nestled amongst the hills.

This walking tour features a meticulously designed itinerary highlighting the best of the Chianti region without feeling hurried or overwhelmed. You’ll indulge in a leisurely, well-paced walk each day, with plenty of time to delve into each location and absorb the scenery.

You’ll have the chance to sample some of the world-famous wines of the Chianti region, pausing at local wineries for a glass or two. The walking paths meander through forests and vineyards, offering awe-inspiring views, with your daily outings punctuated by visits to historical landmarks like the church of Santa Maria Novella.

And the cherry on top?

Our team handles every detail, from securing accommodations to providing GPS tracks for each route and a written guidebook to assist you. We offer round-the-clock support and coordinate transfers to ensure a seamless experience.

Unleash your adventurous spirit and immerse yourself in the awe-inspiring beauty of the Chianti region, where paradise awaits to be discovered and cherished!


Start planning today!

The sooner the better - guaranteed availability and best prices if you don't wait for too long.
Inquire now

Things to know

Book now for guaranteed availability!

Start planning your trip as soon as possible. Flexible booking and Covid Refund Guarantee.
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Those who like a good adventure and limitless flexibility should go on a self-guided tour. We prepare the itinerary and book your accommodations while you enjoy the journey without our guide, being fully in charge of all the daily decisions. While you’ll have the full support of our team in case of any emergencies or concerns, a certain level of self-reliance is required.

Private Guided

Experience the great outdoors on a private guided tour tailored just for you. The tour is for those who want a hastle-free adventure and enjoy the flexibility of a small private group and not stress about the details of everyday planning. The guide will be fully at your disposal to make this experience as personalized as possible, maximizing the enjoyment during and after the tour.

Join a Group

For solo hikers or hikers who wish to meet other like-minded souls, don’t want to stress about tour-planning and other annoying details. We’re going to find you a group of like-minded outdoor enthusiasts and take care of all the other details. The tour will be led by our guide, who’ll make sure everything runs smoothly, ensuring maximum hiking enjoyment.


We handle itineraries, accommodations, and anything else you prefer not to deal with, so you can enjoy a carefree hike.


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


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


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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