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Tuscany Walking Holidays

Walking tours under the Tuscan sun

Tuscany Walking Tours

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Walking on Tuscan path
Sant Antimo Montalcino church and olive tree. Orcia, Tuscany, It
Beautiful alley in Tuscany, Old town Montepulciano, Italy
relaxed adventure woman hiker hiking in Tuscany
Crete senesi
Aerial view over city of Siena
Casale Marittimo village, vineyards and landscape in Maremma. Tuscany, Italy.
Scenic view of Montichiello, Siena, Italy
9 days / 8 nights
Unearth the tranquil allure of Italy's heartland from Montepulciano to Siena, a sensory journey through time-honoured towns and idyllic landscapes.
From: 1,989€/person
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female hiker walking across tuscany 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
Chianti hills with vineyards and cypress. Tuscan Landscape between Siena and Florence. Italy
Culinary delights in siena
Woman is walking in a tuscan countryside
Sunset view of Florence and Duomo. Italy
Siena city skyline, countryside and rolling hills. Tuscany, Italy
Uffizi Gallery. Piazza degli Uffizi square in the early Sunny autumn morning. Florence, Tuscany, Italy
8 days / 7 nights
Leisurely to Moderate
Embark on a journey through the Chianti region, a land renowned for its artistic heritage, architectural marvels, delectable wines, and unique landscapes.
From: 945€/person
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San Miniato bell tower of the cathedral. Pisa, Tuscany Italy Europe.
Pellegrini in cammino lungo la Via Francigena
Monteroni d'Arbia, route of the via francigena. Winding road. Siena, Tuscany. Italy
Landscape along via Francigena with Mud road, fields, trees and vineyard.  Sign showing the direction of Monteroni d'Arbia, route of the via francigena. Siena province, Tuscany. Italy, Europe.
Beautiful view of Dome and campanile of Siena Cathedral, Duomo di Siena, and Old Town of medieval city of Siena at gorgeous sunset, Tuscany, Italy
Pilgrims walking on the path to San Gimignano trough woods and yellow bushes. Solo Backpacker Trekking on the Via Francigena from Lucca to Siena. Walking between nature, history, churches,
Abbadia Isola, Monteriggioni - Toscana
San Gimignano - Toskana
9 days / 8 nights
Moderate to Challenging
Experience the timeless beauty of Tuscany on the historic Via Francigena, a journey through picturesque landscapes, charming hamlets, and UNESCO-listed towns.
From: 1,045€/person
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Siena city skyline, countryside and rolling hills. Tuscany, Italy
Cortona, Calcinaio Church
Medieval Street
Trasimeno lake panoramic view,Castiglione del lago fortress, Umbria, Italy
Scenic Tuscany landscape at sunrise, Val d'Orcia, Italy
Oak barrels in an old wine cellar.
Perugia Via dell Acquedotto
10 days / 9 nights
Discover Italy's heartland on foot, strolling through vineyards, exploring mediaeval towns, and savouring local delicacies across Tuscany and Umbria.
From: 2,089€/person
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One Man hiker hiking alone climbing down a steep mountain path in winter. Taken from distance. Matte high contrast effect
View of the Apuan Alps from the Pisa Tower - Italy
Alpi Apuane view from Monte Prana - Pania secca and Pania di Corfino
Blick auf die Alte Brücke und die Altstadt von Castelnuovo di Garfagnana in der Toskana in Italien
Vagli di Sotto village on Lago di Vagli, Vagli lake, Tuscany, It
smiling woman in floral dress exploring attractions
Idyllic landscape with the village of Poggio and the Apuan Alps in the background. Province of Lucca, Tuscany, central Italy.
Alpi Apuane, trekking sul M. Altissimo 2
8 days / 7 nights
Leisurely to Moderate
Experience the embrace of luxury in Tuscany's hidden gem, the valley of Garfagnana, with our meticulously curated self-guided walking holidays.
From: 2,239€/person
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About Tuscany Walking Holidays

Step into the world of Tuscany Walking Holidays, where the rolling hills whisper tales of the past and the cypress trees sway in rhythm with the wind.

Our walking holidays are tailored to suit every pace and preference — from demanding to easy walking holidays in Tuscany. Whether you’re seeking a leisurely stroll through the vineyards of Chianti or a more challenging hike up the rugged hills of the Apuan Alps, we’ve got you covered.

So, stop and think for a minute: isn’t it about time that you experience the authentic tastes of Tuscany, from the famous Pecorino cheese of Pienza to the exquisite wines of Montepulciano?

We’ll handle all the logistics, from booking comfortable accommodations to arranging transfers for you and your luggage. As such, you can immerse yourself in the local culture without a worry in the world.

On our self-guided walking tours in Tuscany, we equip you with a personalised booklet containing a detailed itinerary, GPS navigation for your hikes, and recommendations for the best local experiences.

Or, we can provide a guide upon request. With Tuscany Walking Holidays, stress-free travel isn’t just a promise — it’s a guarantee.

Tuscany’s Must-Visit Towns

1. Florence

Sunset view of Florence and Duomo. Italy

The cradle of the Renaissance, Florence is a treasure trove of art and architecture.

2. Siena

Piazza del Campo in Siena

Known for its mediaeval brick buildings and the famous Palio horse race, Siena is a step back in time.

3. Montepulciano


Nestled among rolling hills, Montepulciano is renowned for its Renaissance architecture and exquisite wine.

4. Pienza

Spectacular Tuscany cityscape and blooming red poppies, Pienza, Italy, Europe

A UNESCO World Heritage site, Pienza is a jewel of Renaissance architecture with stunning views of the Val d’Orcia and the best Pecorino cheese in the entire Italy.

5. San Gimignano

Vineyards of San Gimignano, Tuscany, Italy

Known as the Manhattan of the Middle Ages, San Gimignano’s skyline is punctuated by towering mediaeval skyscrapers.

The Allure of Walking in Tuscany

Tuscany, a region steeped in history and culture, is a tapestry of ancient townsvineyard-laden hills, and sun-drenched fields. Picture yourself wandering through the cobblestone streets of Florence, the heart of the Renaissance, or exploring the mediaeval charm of Siena, where every street is a journey back in time.

This is the land of the Renaissance, Chianti wine, and landscapes that have inspired artists for centuries — from Leonardo da Vinci to Michelangelo.

As you pass through the ancient villages, you’ll be captivated by the rich tapestry of history unfolding before your eyes. Each stone, each path, and each building tells a story of a time long past yet still very much alive in the hearts and minds of the locals. Just imagine stepping into the world of Tuscany, a world where history whispers in the wind and beauty blooms in every corner.


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.

Things to know

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[email protected]
+386 51 666 500
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Experience the enchanting mediaeval towns, luscious cuisine, and rolling vineyard landscapes with Tuscany Walking Holidays, your gateway to Italian adventures.
Portfolio company of World Discovery.