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

March - October

Technical level

1/5

Fitness level

3/5

Tour type

Inn-to-Inn

Choose your style

Samo Korelec
Samo
Travel Expert
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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 upgrade
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!

Map

Frequently Asked Questions

Of course. We aim to make your decision as easy as possible. Therefore, we crafted several selections targeted at particular groups of hikers – Best for Beginners, Best for Advanced Hikers, Mountain Hikes, Pilgrimages, Classic Treks, etc. 


If you remain unsure and overwhelmed, you can fill out this form or book a call with us, and we can help you directly.

The sooner, the better! Booking in advance ensures you secure a spot, especially on popular routes where accommodations in remote areas can fill up quickly. For tours like the Tour du Mont Blanc and Alta Via, it's best to book several months ahead, as these areas have limited availability in mountain huts.


However, for some of our less-traveled tours, it's possible to book just a few weeks in advance, though availability and comfort may be more limited, particularly in remote areas with fewer options. To ensure you have the best experience, we always recommend booking early, especially during peak hiking seasons.

Our tours offer flexible starting days, allowing you to begin whenever suits you. However, for some of our most popular routes, like the Tour du Mont Blanc (TMB) and Alta Via, we have selected departure days due to high demand and pre-booked accommodations. Be sure to check the specific requirements for these tours.

We offer a variety of tours suitable for different fitness levels and technical abilities. Some of them require no prior hiking experience.


Whether you’re a beginner or an experienced hiker, we have the perfect route for you. You can find more information in our Hiking Difficulty Guide, and we also have dedicated sections for Best for Beginners and Best for Advanced Hikers to help you choose the suitable tour.

The fitness level is based on a scale determined by our hiking experts. It varies depending on the tour and defines the selected hiking tour's physical requirements in comparison to others. For a detailed overview, please refer to our Hiking Difficulty Guide. 

The technical demands of each hike differ. The technical-level scale defines the technical requirements of each tour in comparison to others, ranging from basic walking to scrambling or using specialized equipment. For a more in-depth explanation of the five levels, please refer to our Hiking Difficulty Guide.

Most of our tours are self-guided, meaning you have the freedom to explore at your own pace without being tied to a group schedule. We provide detailed digital guidebooks that include maps, route notes, and GPS files to ensure a smooth experience.


You can learn more about the concept by reading Self-Guided Tours Explained. We include a guide only for the most challenging treks, like the Triglav Summit Climb.

We provide a comprehensive digital guidebook with maps, route notes, accommodation details, and emergency contacts. Our support will be available during the tour. However, you'll have all the information you need to enjoy your hike independently.


Check out how self-guided tours work in more detail and an example of our digital guidebook here.

Ratings & Reviews

Google Reviews

5.0 average rating

Carly Leonard's profile photo
Michael White's profile photo
Roman Klymenko's profile photo
Birgit Kindler's profile photo
Dominik Schrotter's profile photo
+45
Top Rated Brand
Carly Leonard's profile photo

Carly Leonard

Verifed customer · 1 year ago

My friend and I went with Triglav Tours for a 3 day, 2 night hike this summer and had the most amazing time!! Our guide, Bine, was awesome and had lots of cool facts to share about the area we were hiking. Additionally, my friend and I had not completed such a technical hike before and the guide and other guests were very patient with us and encouraging, ensuring we felt safe the entire time. The overnights were also such a fun way to get to know Bine, the other guests, and other hikers as well. Cannot recommend Triglav tours enough!!!

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Michael White

Verifed customer · 1 year ago

I arranged a six-day/five-night trip with Hut to Hut Slovenia. It's the first time I've gone with a tour organizer and I can say it went really well. In the past I've arranged huts myself and it is a huge hassle figuring out how to make the bookings, if the bookings actually exist, and what good/viable routes might be. Having this all sort was, at least to me, totally worth it. The routing is via Ride with GPS, which was great. I'd recommend bringing 1:25,000 scale paper maps as a backup, just in case. The huts themselves differ wildly. Some are really rustic with, ahem, interesting toilet facilities. One was accessible by road and thus had showers, a long menu, and even espresso. All will have some sort of food, but you might only have two options for dinner (one with meat, one vegetarian). The cuisine in the Slovenian huts leans strongly to stews and goulashes with minimal fresh vegetables and/or fruit. Certainly good and hearty but pretty much everyone I talked to said the food was better in the Italian and Austrian huts. Some huts are cash only, some take cards (but the card reader might be down). A 1.5 litre bottle of water is about 6 euro, so if you have a beer with dinner and also buy lunch you need to carry about 25-30 euro per day in cash (assuming you have a booking that includes breakfast). Of the six days of hiking, four were ridiculously spectacular, with the highlight being sunrise from Mt Stol. Getting up to the high mountains, though, can be crazy steep, with switchbacks only sparsely used. Descents are similarly tough, and you have to watch every step. For the first time ever I used trekking poles and my knees thank me. Two days were a bit of a slog, but this is probably unavoidable getting up to or down from the high terrain. Would I do something like this again? Yes, absolutely! But next time it will probably be the Dolomites.

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Roman Klymenko

Verifed customer · 1 year ago

Very beautiful hike. I did not expect that Slovenia is so amazing.

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Birgit Kindler

Verifed customer · 1 year ago

We had a lovely hike today with our guide Klemen. He personalized the tour on our needs and interests, so that we saw places we wouldn't without his experience. The hike was a little bit slippery after the rain from the last days and it went a lot upwards, but it was totally worth it! Thanks again :)

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Dominik Schrotter

Verifed customer · 1 year ago

We had a great day with Klemen on this hike, he showed us some lesser known spots/highlights of the southern part of the julian alps with a nice viewpoint at the end. 10/10 would book again

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Gisela Irion

Verifed customer · 1 year ago

Tina and her team gave me perfect support on my hut hike through the Triglav National Park in July. In particular, they had to cater to my specific needs twice, which they did for me with no problem. I once had to cancel at short notice before the start of the trip because my father was not feeling well, but then we found a solution and I was able to start the hike. Tina and team first canceled the huts immediately and then reserved them again for me. Even when my condition caused a little tour change again, I immediately had suggestions and these were immediately available in the Trip plans app. I liked this app very much because it was easy to handle and the huttohut-team gave a short overview how the daily tour will be and which highlights – mostly beautiful views – I will see“

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