Background Image

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
Siena
Finish point
Florence
Duration
10 days / 9 nights
Season
Mar - Nov
Price
From: 2,089€/person
Difficulty
Leisurely
Suitable for everybody who enjoys an occasional walk
Inquiry

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
Siena
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

Optional Extras

Transfer to and from the airport
Single supplement
Wine Tasting
From:
2,089€
/person
Inquiry

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?

Map

Start planning today!

The sooner the better - guaranteed availability and best prices if you don't wait for too long.
Inquire now

Things to know

Book now for guaranteed availability!

Start planning your trip as soon as possible. Flexible booking and Covid Refund Guarantee.
Inquire now

Self-guided

Those who like a good adventure and limitless flexibility should go on a self-guided tour. We prepare the itinerary and book your accommodations while 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.

Private Guided

Experience the great outdoors on a private guided tour tailored just for you. The tour is for those who want a hastle-free adventure and enjoy the flexibility of a small private group and not stress about the details of everyday planning. The guide will be fully at your disposal to make this experience as personalized as possible, maximizing the enjoyment during and after the tour.

Join a Group

For solo hikers or hikers who wish to meet other like-minded souls, don’t want to stress about tour-planning and other annoying details. We’re going to find you a group of like-minded outdoor enthusiasts and take care of all the other details. The tour will be led by our guide, who’ll make sure everything runs smoothly, ensuring maximum hiking enjoyment.

HASSLE-FREE

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.

TRIED & TESTED ADVENTURES

Only the best walking tours in Tuscany, cherry-picked by our 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.

Similar Tuscany Walking Tours

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
Moderate
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
More →
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
More →
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
More →
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
More →
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.