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












Montepulciano to Siena Walking Holidays
9 days / 8 nights
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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
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!
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Self-guided
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