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Walking Holidays in Tuscany and Umbria

Discover Italy's heartland on foot, strolling through vineyards, exploring mediaeval towns, and savouring local delicacies across 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

Stroll through the historic streets of Siena, a UNESCO World Heritage Site

Savour the renowned wines of Montepulciano

Discover Pienza, a gem of Renaissance architecture

Enjoy breathtaking views from the hilltop town of Cortona

Explore the vibrant city of Perugia, rich in history and culture

Immerse yourself in the art and architecture of Florence, the cradle of the Renaissance

Siena city skyline, countryside and rolling hills. Tuscany, Italy

Explore the Tuscan and Umbrian towns

Cortona, Calcinaio Church

Uncover the secrets of scenic villages

Medieval Street

Stroll through history in Tuscany's streets

Trasimeno lake panoramic view,Castiglione del lago fortress, Umbria, Italy

Soak in the serenity of Lake Trasimeno

Scenic Tuscany landscape at sunrise, Val d'Orcia, Italy

Savour the beauty of the region at sunrise

Oak barrels in an old wine cellar.

Sample renowned Montepulciano wines

Perugia Via dell Acquedotto

Immerse yourself in the historic sights of Umbria


Revel in the grandeur of Siena

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


Can we paint a picture for you?

You’re meandering through a patchwork of vineyards, their ripe grapes glistening under the Tuscan sun. The gentle undulation of the emerald hills stretches out before you, a living canvas of Italy’s heartland. On the horizon, the stone towers of a mediaeval town rise, whispering tales of yesteryears and inviting you to uncover their secrets.

These are the Walking Holidays in Tuscany and Umbria, in essence.

Your journey will take you through the charming towns of Siena, Montepulciano, Pienza, Cortona, Perugia, and Florence. Each town, a treasure trove of history, art, and culture, offers its unique charm.

From Siena’s shell-shaped Piazza del Campo to the Renaissance beauty of Pienza. From the hilltop town of Cortona to the vibrant city of Perugia and finally to Florence, the cradle of the Renaissance.

The hikes are leisurely, allowing ample time to soak in the scenery, delve into the local culture, and truly experience the Italian way of life. You’ll walk through some of the most picturesque cities in Tuscany and Umbria, with plenty of time to discover hidden gems, sample local delicacies, and simply sit back and enjoy the view.

We oversee and book all the accommodations, ensuring you have a comfortable place to rest after a day of exploration. We provide a detailed handout with a day-by-day itinerary, complete with GPS navigation via a user-friendly app.

You’ll also receive local recommendations to help you discover the best each town has to offer. And if any logistical issues arise, we’re here to solve them, so you can focus on enjoying your holiday.

Are you ready to swap your office chair for a seat in a quaint Italian café, your daily commute for a walk through sun-drenched vineyards, and your alarm clock for the tolling of a mediaeval bell tower? After all, why just visit Italy when you can walk it?


Start planning today!

The sooner the better - guaranteed availability and best prices if you don't wait for too long.
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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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For travellers that want flexibility and independence. We organize the tours of your choice, but the adventure of getting around is all yours. You will get a fly & drive itinerary handout with activities, accommodations and travelling tips with full support of our team for any emergencies or concerns. You will take yourself around Slovenia, but we can arrange a car rental or even a campervan if you wish.


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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Experience the enchanting mediaeval towns, luscious cuisine, and rolling vineyard landscapes with Tuscany Walking Holidays, your gateway to Italian adventures.
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