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Tuscany Walking Tours

Explore the breathtaking landscape of Tuscany through expertly crafted walking tours that showcase the beauty of the lush green hills and medieval towns.
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9 days / 8 nights
Discover the serene beauty of Italy's core on a journey from Montepulciano to Siena, a captivating trek through historic towns and picturesque scenery.
From: 1,989€/person
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9 days / 8 nights
Moderate to Challenging
Discover the enduring allure of Tuscany along the historic Via Francigena, taking you through scenic vistas, quaint villages, and towns recognized by UNESCO.
From: 1,045€/person
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10 days / 9 nights
Experience the soul of Italy by walking through its scenic vineyards, visiting ancient towns, and indulging in regional treats in both Tuscany and Umbria.
From: 2,089€/person
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8 days / 7 nights
Indulge in the lap of luxury with our carefully crafted self-guided walking holidays in Tuscany's lesser-known treasure, the Garfagnana Valley.
From: 2,239€/person
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8 days / 7 nights
Leisurely to Moderate
Stroll the land of artistry, finest architecture, savory wine, and heavenly landscape on this walking tour across the Chianti region of Tuscany.
From: 945€/person
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About Tuscany Walking Tours

Tuscany is a picturesque region in central Italy renowned for its charming countryside, artistic heritage, and gastronomic delights. If you’re seeking a peaceful retreat in the heart of Italy, you can find the perfect itinerary among our Tuscany walking tours.

Get on a journey of discovery as you explore quaint villages, verdant hills, and medieval towns. You’ll be enchanted by the vineyards of Chianti, the cypress-lined roads, the medieval city of Siena, and the Renaissance gem of Florence.

Our walking tours in Tuscany cater to all fitness levels and interests, ensuring an enjoyable exploration of the region’s ethereal charm at your own pace. While we handle all the logistics, you can relax and immerse yourself in the local culture.

You’ll have the opportunity to learn about wine-making, olive oil production, and Tuscan cuisine. From visiting the cellars of “azende agricole” to sampling the famous Pecorino cheese of Pienza, you’ll experience the authentic tastes of Tuscany.

Before your trip, we’ll provide you with a personalized booklet containing a day-by-day itinerary, detailed descriptions of your hikes, and recommendations for the best local experiences. We’ll also equip you with GPS navigation and book all your accommodations. Stress-free travel, you say?

There is really nothing more we could say about Tuscany. You just have to experience it in person. We are just a couple of clicks on our inquiry page away.


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

Trusted by Many

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

Handpicked Adventures

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

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.
Towering rock faces of the Dolomites, Tuscany’s unique architecture, and charming towns on the Amalfi Coast — discover it all on walking holidays in Italy!
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Portfolio company of World Discovery.