15 km and 470 m of elevation gain / 520 m of elevation loss












Montepulciano to Siena Walking Holidays
9 days / 8 nights
|
Starting point
Montepulciano
Finish point
Siena
Season
From March to October
Technical level
1/5
Fitness level
3/5
Tour type
Inn-to-Inn


Starting point
Montepulciano
Finish point
Siena
Season
From March to October
Technical level
1/5
Fitness level
3/5
Tour type
Inn-to-Inn
- 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
Itinerary of the trip
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What’s included in the price?
Self-guided
NOT INCLUDED
OPTIONAL EXTRAS
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
Ratings & Reviews

5.0 average rating






We had an incredible time on the 5 day hut to hut hike in Croatia. The views were perfect, the accommodation much nicer than we imagined and we had a fantastic support guide - Ivan - who was very friendly and made the whole trip possible. We were also able to go to the beach most days after we finished our hiking and everything was very flexible. I would highly recommend this to anyone.


1) Stunningly beautiful places with perfect weather! Good balance of countryside and old city walking. 2) The Trip App was incredible!!! 5 stars! Loved the write ups on each location. The links to all restaurants, hotels, attractions, tickets! The GPS app also worked. 3) PERFECTLY located hotels and rooms with two beds and thoughtful staff! Loved being right in the old towns with amazing views. I did not mind carrying bags up or down in order to have the locations but much appreciated when we did have help with this 4) Breakfast being included with the rooms (even though there was a mix up the first morning). I don't like to have to plan breakfast spots and the buffets were incredible. 5) The kindness and promptness of the drivers, Nice transport vehicles and easy drop off and pick up points. Plus help with our bags. 6) The Walking Holidays Croatia team was helpful and easy to work with. We appreciate all they did to customize out trip.


Tour was very well organised with lots of information to help guide us through the holiday. All the accommodation was great. Particularly liked the self catering Glamping Mountain Fairytale and the Berghi Hotel. Food at the Hotel Starkl restaurant was great as well. The route took us through a beautiful part of the country on quiet roads and cycle paths. The cycle paths are much better than in the UK and I would also like to say that Slovenian car drivers are much more patient and tolerant than many drivers in the UK. Beautiful country. Really enjoyed it.
Walking the GR10 was an incredible way to experience the Pyrenees. Each day brought something different—lush valleys, high mountain passes, and charming villages. The huts provided a warm bed, great meals, and a chance to meet fellow hikers. The clear itinerary and support from Hut to Hut Hiking Europe made it easy to focus on enjoying the trail. I’d recommend this hike to anyone looking for a multi-day trek with lots of variety.
My walking holiday in Chamonix and the French Alps was unforgettable. Each day brought stunning views of towering peaks, alpine meadows, and glacial streams. The routes were well-marked and varied in difficulty, making it easy to tailor the days to my pace. The accommodations were charming and perfectly situated for breathtaking morning views. Lan was so helpful in suggesting how to make the most of my time in the region, and their support made the whole trip seamless. If you love mountains and fresh air, this trip is a must!
My walking holiday in Chamonix and the French Alps was unforgettable. Each day brought stunning views of towering peaks, alpine meadows, and glacial streams. The routes were well-marked and varied in difficulty, making it easy to tailor the days to my pace. The accommodations were charming and perfectly situated for breathtaking morning views. Lan was so helpful in suggesting how to make the most of my time in the region, and their support made the whole trip seamless. If you love mountains and fresh air, this trip is a must!
We had an incredible time on the 5 day hut to hut hike in Croatia. The views were perfect, the accommodation much nicer than we imagined and we had a fantastic support guide - Ivan - who was very friendly and made the whole trip possible. We were also able to go to the beach most days after we finished our hiking and everything was very flexible. I would highly recommend this to anyone.


Tour was very well organised with lots of information to help guide us through the holiday. All the accommodation was great. Particularly liked the self catering Glamping Mountain Fairytale and the Berghi Hotel. Food at the Hotel Starkl restaurant was great as well. The route took us through a beautiful part of the country on quiet roads and cycle paths. The cycle paths are much better than in the UK and I would also like to say that Slovenian car drivers are much more patient and tolerant than many drivers in the UK. Beautiful country. Really enjoyed it.
My walking holiday in Chamonix and the French Alps was unforgettable. Each day brought stunning views of towering peaks, alpine meadows, and glacial streams. The routes were well-marked and varied in difficulty, making it easy to tailor the days to my pace. The accommodations were charming and perfectly situated for breathtaking morning views. Lan was so helpful in suggesting how to make the most of my time in the region, and their support made the whole trip seamless. If you love mountains and fresh air, this trip is a must!
1) Stunningly beautiful places with perfect weather! Good balance of countryside and old city walking. 2) The Trip App was incredible!!! 5 stars! Loved the write ups on each location. The links to all restaurants, hotels, attractions, tickets! The GPS app also worked. 3) PERFECTLY located hotels and rooms with two beds and thoughtful staff! Loved being right in the old towns with amazing views. I did not mind carrying bags up or down in order to have the locations but much appreciated when we did have help with this 4) Breakfast being included with the rooms (even though there was a mix up the first morning). I don't like to have to plan breakfast spots and the buffets were incredible. 5) The kindness and promptness of the drivers, Nice transport vehicles and easy drop off and pick up points. Plus help with our bags. 6) The Walking Holidays Croatia team was helpful and easy to work with. We appreciate all they did to customize out trip.


Walking the GR10 was an incredible way to experience the Pyrenees. Each day brought something different—lush valleys, high mountain passes, and charming villages. The huts provided a warm bed, great meals, and a chance to meet fellow hikers. The clear itinerary and support from Hut to Hut Hiking Europe made it easy to focus on enjoying the trail. I’d recommend this hike to anyone looking for a multi-day trek with lots of variety.
My walking holiday in Chamonix and the French Alps was unforgettable. Each day brought stunning views of towering peaks, alpine meadows, and glacial streams. The routes were well-marked and varied in difficulty, making it easy to tailor the days to my pace. The accommodations were charming and perfectly situated for breathtaking morning views. Lan was so helpful in suggesting how to make the most of my time in the region, and their support made the whole trip seamless. If you love mountains and fresh air, this trip is a must!
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