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Montepulciano to Siena Walking Holidays

Unearth the tranquil allure of Italy's heartland from Montepulciano to Siena, a sensory journey through time-honoured towns and idyllic landscapes.
Starting point
Finish point
9 days / 8 nights
Mar - Nov
From: 1,989€/person
Suitable for most active people with with good stamina and basic walking experience

Stroll through the vineyards and olive groves of Tuscany

Explore the mediaeval charm of hilltop towns like Montepulciano and Siena

Savour the flavours of local cuisine and world-renowned wines

Experience the tranquillity of the peaceful village of Montichiello

Marvel at the stunning views of the iconic Tuscan scenery from the hilltop town of Pienza

Visit the isolated Sant’ Antimo Abbey, a gem of Romanesque architecture

Walking on Tuscan path
Discover Italy's heartland on foot through Tuscany
Sant Antimo Montalcino church and olive tree. Orcia, Tuscany, It
Marvel at Sant' Antimo's Romanesque architecture
Beautiful alley in Tuscany, Old town Montepulciano, Italy
Delve into Montepulciano's mediaeval charm
relaxed adventure woman hiker hiking in Tuscany
Seek tranquil adventure in Tuscany's scenic trails
Crete senesi
Immerse in the unique landscapes of Crete Senesi
Aerial view over city of Siena
Behold the architectural marvel of Siena
Casale Marittimo village, vineyards and landscape in Maremma. Tuscany, Italy.
Wander through Tuscany's sun-kissed vineyards
Scenic view of Montichiello, Siena, Italy
Experience the tranquillity of hilltop Montichiello

Included in price

Tour design and organisation

24/7 service and support during your holidays

GPS navigation with an easy-to-use app

7x accommodation with breakfast in 3/4* hotels

Luggage transfer

Optional Extras

Transfer to and from the airport
Single supplement

Step into a world where time slows down, where the sweet life, or ‘la dolce vita,’ isn’t just a phrase but a way of being. It’s time for a journey that takes you to the heart of Italy, not through the hustle and bustle of its cities but through the serene beauty of the Tuscan countryside. Here, the charm of mediaeval hilltop towns competes with the allure of sunflower fields, olive groves, and rolling vineyards.

Your adventure will take you through some of the most picturesque towns in Tuscany, from the wine-lovers paradise of Montepulciano to the architectural marvel of Siena. Along the way, you’ll discover the Renaissance splendour of Pienza, the tranquil beauty of Castelnuovo dell’Abate, and the mediaeval charm of Lucignano, among others.

Each town is a gem waiting to be explored, set against the backdrop of Tuscany’s iconic rolling hills and cypress-lined roads.

Our walking holidays are designed with leisure in mind. The hikes are gentle, the pace is relaxed, and there’s plenty of time to explore on your own. You’ll traverse some of the most scenic parts of the Via Francigena, an ancient pilgrimage route, and focus on the most picturesque cities between Montepulciano and Siena.

At Tuscany Walking Holidays, we take care of all the details so you can focus on enjoying your holiday. We oversee the accommodation availability and secure all the bookings, provide a detailed written handout with a day-by-day itinerary, and offer GPS navigation with a user-friendly app.

So, are you ready to swap your office chair for a seat at a Tuscan trattoria, your daily commute for a stroll through a vineyard, and your alarm clock for the morning sun streaming through your window? Come and lose yourself in the Tuscan countryside with us.


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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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.


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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