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Montepulciano to Siena Walking Holidays

Discover the serene beauty of Italy's core on a journey from Montepulciano to Siena, a captivating trek through historic towns and picturesque scenery.
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

Wander amidst Tuscany’s olive orchards and vineyards

Delight in the culinary offerings and famous vintages of the region

Experience the calm ambiance of the quiet village of Montichiello

Take in breathtaking panoramas of classic Tuscan landscapes from the elevated town of Pienza

Discover the secluded Sant’ Antimo Abbey, a masterpiece of Romanesque design

Uncover the mediaeval allure of elevated towns like Montepulciano and Siena

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Discover Italy's heartland on foot through Tuscany

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Marvel at Sant' Antimo's Romanesque architecture

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Delve into Montepulciano's mediaeval charm

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Seek tranquil adventure in Tuscany's scenic trails

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Immerse in the unique landscapes of Crete Senesi

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Behold the architectural marvel of Siena

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Wander through Tuscany's sun-kissed vineyards

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Experience the tranquillity of hilltop Montichiello

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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

7x accommodation with breakfast in 3/4* hotels

Luggage transfer

Enter a realm where the clock ticks slower, where the famed ‘la dolce vita’ is not merely a saying but a lifestyle. Prepare for an expedition that leads you into Italy’s soul, bypassing the urban frenzy to bask in the tranquil allure of the Tuscan landscapes. Here, the enchantment of ancient hilltop villages rivals the beauty of sprawling sunflower meadows, olive orchards, and vine-laden hills.

Your journey will guide you through some of Tuscany’s most visually stunning towns, from Montepulciano, a haven for wine aficionados, to Siena, a city that’s an architectural wonder. En route, you’ll encounter the Renaissance elegance of Pienza, the peaceful allure of Castelnuovo dell’Abate, and the mediaeval magnetism of Lucignano, to name a few.

Our walking holidays prioritise your comfort and leisure. The trails are easygoing, the tempo is unhurried, and ample free time is built in for personal exploration. You’ll navigate some of the most picturesque segments of the Via Francigena, an age-old pilgrimage trail focusing on the most scenic towns between Montepulciano and Siena.

At Tuscany Walking Holidays, we manage all the intricacies so you can concentrate on relishing your vacation. We handle accommodation arrangements, furnish you with a comprehensive, written day-to-day plan, and supply GPS guidance through an intuitive app.

So, are you set to exchange your desk chair for a cosy spot in a Tuscan eatery, your daily drive for a leisurely walk amid vineyards, and your morning alarm for the first rays of sunlight filtering through your window? Come discover the Tuscan landscapes with us.


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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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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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