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
Starting point
Montepulciano
Finish point
Siena
Season
From March to October
Technical level
1/5
Fitness level
3/5
Tour type
Inn-to-Inn
Highlights
- 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
We had great experience with the Triglav Tours team. They were always available, responsive and helpful. They arranged our trip during high season and managed to find solutions were other agencies did not. Thank you Eva and the entire Triglav Tours team!
I have a lot of experience hiking in the mountains but still chose to book a guide, as I have neither the gear nor experience in via ferrata climbing. It turned out to be a really good idea! Prior to the trip, I had contact with the organizer and a video call where I could ask questions, which provided a good basis for deciding which trip was right for me. We were three women + our guide Jakob. On day 2, we started very early before sunrise, which gave us a bit more space on the trail and the pleasure of watching the sun rise over the mountain. Jakob was incredibly good at making our small group function, even though our levels were quite varied. I have a fear of heights, but I didn't feel unsafe at all. It was really nice that there was time to clip us into the wire. Back at the cabin, we had breakfast before heading back down towards the car. An absolutely fantastic trip that requires good physical fitness.
The Tour du Mont Blanc was easily one of the most memorable trips I’ve taken in years. From breathtaking views and warm, welcoming people to delicious food and charming mountain huts, every aspect of the journey was unforgettable. The hikes were significantly more challenging than I had anticipated, but the reward was well worth the effort. I can’t overstate how much smoother and more stress-free the experience was thanks to Hut to Hut’s incredibly detailed guides. Having accommodations pre-booked, access to a well-designed GPS trail map, and a comprehensive guide outlining what to expect, what to pack, and what to watch out for made all the difference. If you’re considering hiking the TMB, I wholeheartedly recommend booking with Hut to Hut. Their support turned a great adventure into an exceptional one.
We had great experience with the Triglav Tours team. They were always available, responsive and helpful. They arranged our trip during high season and managed to find solutions were other agencies did not. Thank you Eva and the entire Triglav Tours team!
I have a lot of experience hiking in the mountains but still chose to book a guide, as I have neither the gear nor experience in via ferrata climbing. It turned out to be a really good idea! Prior to the trip, I had contact with the organizer and a video call where I could ask questions, which provided a good basis for deciding which trip was right for me. We were three women + our guide Jakob. On day 2, we started very early before sunrise, which gave us a bit more space on the trail and the pleasure of watching the sun rise over the mountain. Jakob was incredibly good at making our small group function, even though our levels were quite varied. I have a fear of heights, but I didn't feel unsafe at all. It was really nice that there was time to clip us into the wire. Back at the cabin, we had breakfast before heading back down towards the car. An absolutely fantastic trip that requires good physical fitness.
The Tour du Mont Blanc was easily one of the most memorable trips I’ve taken in years. From breathtaking views and warm, welcoming people to delicious food and charming mountain huts, every aspect of the journey was unforgettable. The hikes were significantly more challenging than I had anticipated, but the reward was well worth the effort. I can’t overstate how much smoother and more stress-free the experience was thanks to Hut to Hut’s incredibly detailed guides. Having accommodations pre-booked, access to a well-designed GPS trail map, and a comprehensive guide outlining what to expect, what to pack, and what to watch out for made all the difference. If you’re considering hiking the TMB, I wholeheartedly recommend booking with Hut to Hut. Their support turned a great adventure into an exceptional one.
All available guidance options
Self-guided
Those who like a good adventure and limitless flexibility should go on a self-guided tour...
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