
Tuscany Walking Holidays
Tuscany Walking Tours

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
The cradle of the Renaissance, Florence is a treasure trove of art and architecture.
2. 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
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
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 towns, vineyard-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.
HASSLE-FREE
TRUSTED BY MANY
TRIED & TESTED ADVENTURES
UNBEATABLE SUPPORT
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