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
Choose your style
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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
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.


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!
My walking holiday in Brittany was a peaceful escape. The coastal paths offered stunning views of dramatic cliffs, sandy beaches, and charming fishing villages. The inland trails led through lush forests and past ancient landmarks like standing stones and medieval chapels. Samo and Anja made planning so easy with their detailed itineraries and helpful advice. The accommodations were cozy and full of local character, and I loved being able to sample the region’s incredible seafood. Brittany’s beauty is truly timeless!
I did the Fisherman Trail in Portugal mid April and I had a fantastic time. The trip was well organized and the luggage transfer seamless. The maps were clear and easy to navigate, and always got me to my destination safe and sound. And the accommodations felt like a complete splurge, especially the B&B. And of course the views along the trail were amazing. Definitely would recommend booking with them!
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.


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!
I did the Fisherman Trail in Portugal mid April and I had a fantastic time. The trip was well organized and the luggage transfer seamless. The maps were clear and easy to navigate, and always got me to my destination safe and sound. And the accommodations felt like a complete splurge, especially the B&B. And of course the views along the trail were amazing. Definitely would recommend booking with them!
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 Brittany was a peaceful escape. The coastal paths offered stunning views of dramatic cliffs, sandy beaches, and charming fishing villages. The inland trails led through lush forests and past ancient landmarks like standing stones and medieval chapels. Samo and Anja made planning so easy with their detailed itineraries and helpful advice. The accommodations were cozy and full of local character, and I loved being able to sample the region’s incredible seafood. Brittany’s beauty is truly timeless!
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Self-guided
Those who like a good adventure and limitless flexibility should go on a self-guided tour...
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