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Montepulciano to Siena Walking Holidays

9 days / 8 nights

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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

Montepulciano

Finish point

Siena

Season

From March to October

Technical level

1/5

Fitness level

3/5

Tour type

Inn-to-Inn

Choose your style

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Samo Korelec
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  • 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

What’s included in the price?

Self-guided

8 nights in 3-star hotels with breakfast
Digital guidebook with itinerary, route instructions, and practical information
GPS navigation with an easy-to-use app
Tour design and organization
Service and support during your hike

NOT INCLUDED

Tourist tax

OPTIONAL EXTRAS

Hotel upgrades
Luggage transfer
Single supplement

What to bring to the tour

  • Hiking shoes/boots
  • 25 to 35-liter backpack
  • Base layer
  • Sports T-shirts
  • Hiking shorts
  • Hiking water-repellent pants
  • Waterproof jacket
  • Midlayer
  • Sports socks and underwear
  • Leisurewear for evenings
  • Shade hat/cap
  • Sunscreen
  • Sunglasses
  • Hiking poles
  • ID card or passport
  • Snacks
  • Cash
  • Water bottles or hydration pack
  • Toiletries

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.

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!

Frequently Asked Questions

Our tours are designed to cater to a broad range of people, but some days can be quite challenging, with long distances and significant elevation gain. We aim to minimize this as much as possible while ensuring a high-quality experience. To fully enjoy our tours, you should be accustomed to walking for 4-6 hours, overcoming around 600 meters of elevation gain.

However, Alta Via 1 hut-to-hut hikes and Tour du Mont Blanc are more demanding and require a higher fitness level. On these tours, you may need to hike up to 8 hours per day and tackle substantial elevation gain.

Yes, our hiking holidays are appropriate for children who are physically prepared and have a good balance. However, to guarantee the safety and enjoyment of our young participants, we suggest that they should be at least eight years old to join our tours.

Proper footwear is crucial for our walking tours. We recommend wearing sturdy hiking shoes with ankle support for all our hikes. The terrain can be uneven, rocky, and slippery. Wearing sneakers can be dangerous, especially if you are not accustomed to hiking on such surfaces, as they do not offer enough protection and support. Robust shoes also provide the necessary support when your legs get tired during long hikes.

Yes, we highly recommend booking in advance to secure your spot. The earlier you book, the better the chances are of getting your preferred options. If you book close to the start of the season or during the season, we may not be able to guarantee availability in the hotels and apartments. Therefore, it is best to make reservations as soon as possible to avoid any inconvenience.

It is essential to note that accommodations at the destinations of our walking tours are in high demand during the summer season. Therefore, early booking is crucial to secure your preferred type of housing. However, we assure you that we will always try our best to provide you with the most suitable lodging based on your preferences. Rest assured that we will do everything possible to ensure that your stay is comfortable and enjoyable.

Our tours are well-organized, and all the destinations are easily accessible and straightforward to navigate. Therefore, it is unlikely that you will require a guide. Our comprehensive handout will provide you with all the essential information while still allowing you the freedom of a self-guided holiday.

However, if you prefer to have a guide, please let us know, and we will make the necessary arrangements for you.

Most of the accommodations we provide offer vegetarian and vegan options for breakfast. Additionally, you will find no shortage of vegetarian and vegan menus in restaurants during the tour. However, it is worth noting that some mountain huts on Alta Via 1 or Tour du Mont Blanc may not offer vegan meals. In such situations, it is advisable to bring your own food to ensure that your dietary needs are met.

The best time to go on a walking holiday in Italy varies depending on the location you plan to visit. Destinations such as the Amalfi Coast, Cinque Terre, and Sicily are best visited during early spring and fall when the weather is pleasant, and the crowds are fewer.

However, in areas like the Dolomites or around Mont Blanc, hiking is not possible when there is snow high up in the mountains. Therefore, the hiking season in these areas is limited from late June to late September. It is advisable to plan your trip accordingly to get the best out of your walking holiday in Italy.

We can best advise you after receiving a filled-out inquiry form.

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Self-guided

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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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from 2.289 € /person