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Walking Holidays in Tuscany and Umbria

Experience the soul of Italy by walking through its scenic vineyards, visiting ancient towns, and indulging in regional treats in both Tuscany and Umbria.
Starting point
Finish point
10 days / 9 nights
Mar - Nov
From: 2,089€/person
Suitable for everybody who enjoys an occasional walk

Dive into Florence’s wealth of art and historical structures, known as the birthplace of the Renaissance

Take in awe-inspiring panoramas from Cortona, perched atop a hill

Relish the celebrated vintages from Montepulciano

Experience the lively atmosphere of Perugia, a city steeped in cultural heritage

Uncover the architectural marvels of Pienza, a jewel of the Renaissance

Wander the age-old lanes of Siena, recognized as a UNESCO World Heritage Site

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Explore the Tuscan and Umbrian towns

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Uncover the secrets of scenic villages

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Stroll through history in Tuscany's streets

Trasimeno lake panoramic view scaled

Soak in the serenity of Lake Trasimeno

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Savour the beauty of the region at sunrise

Montepulciano vino nobile scaled

Sample renowned Montepulciano wines

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Immerse yourself in the historic sights of Umbria

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Revel in the grandeur of Siena

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Included in price

Tour design and organisation

24/7 service and support during your holidays

GPS navigation with an easy-to-use app

9x accommodation with breakfast in 3/4* hotels

Luggage transfer

Transfers as per itinerary

You’re strolling through a mosaic of vineyards, where grapes ripen to perfection under the warm Tuscan sun. The rolling green hills stretch endlessly, forming a vivid backdrop that captures the essence of Italy’s rural heart. Ancient stone towers from mediaeval towns punctuate the horizon, beckoning you to explore their rich history.

This is the essence of Walking Holidays in Tuscany and Umbria.

Your adventure will guide you through captivating towns like Siena, Montepulciano, Pienza, Cortona, Perugia, and Florence. Each location is a repository of history, art, and culture, radiating its own unique allure.

From the iconic Piazza del Campo in Siena to the Renaissance elegance of Pienza; from Cortona’s hilltop vistas to the bustling atmosphere of Perugia, and ultimately to Florence — the epicentre of Renaissance art and architecture.

The walks are relaxed, designed to give you plenty of time to absorb the landscapes, engage with local traditions, and truly live the Italian lifestyle. You’ll traverse some of the most scenic cities and towns in Tuscany and Umbria with ample opportunities to uncover hidden treasures, taste regional foods, and relish the breathtaking views.

We take care of all your accommodation needs, ensuring you have a cosy place to unwind after a day of discovery. A comprehensive guide, complete with day-by-day plans and GPS navigation through an easy-to-use app, will be at your fingertips.

We’ll also offer local tips to enhance your experience in each town. Should any logistical challenges come up, we’re on hand to resolve them, allowing you to concentrate on savouring your vacation.

So, are you prepared to exchange your office environment for the ambiance of a charming Italian café, your daily drive for a leisurely walk amidst sunlit vineyards, and your morning alarm for the chimes of an ancient bell tower?


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Things to know


Those who like a good adventure and limitless flexibility should go on a self-guided cycling holiday in Slovenia. We prepare the itinerary and book your accommodations; 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.


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

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Handpicked Adventures

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

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