14 km and 600 m of elevation gain / 500 m of elevation loss












Walking Holidays in Tuscany and Umbria
10 days / 9 nights
|
Starting point
Siena
Finish point
Florence
Season
From March to November
Technical level
2/5
Fitness level
3/5
Tour type
product_attributes.Travel-And-Hike


Starting point
Siena
Finish point
Florence
Season
From March to November
Technical level
2/5
Fitness level
3/5
Tour type
product_attributes.Travel-And-Hike
- Dive into Florence's wealth of art and historical structures, known as the birthplace of the Renaissance
- Take in awe-inspiring panoramas from Cortona, perched atop a hill
- Relish the celebrated vintages from Montepulciano
- Experience the lively atmosphere of Perugia, a city steeped in cultural heritage
- Uncover the architectural marvels of Pienza, a jewel of the Renaissance
- Wander the age-old lanes of Siena, recognized as a UNESCO World Heritage Site
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
You're strolling through a mosaic of vineyards, where grapes ripen to perfection under the warm Tuscan sun. The rolling green hills stretch endlessly, forming a vivid backdrop that captures the essence of Italy's rural heart. Ancient stone towers from mediaeval towns punctuate the horizon, beckoning you to explore their rich history.
This is the essence of Walking Holidays in Tuscany and Umbria.
Your adventure will guide you through captivating towns like Siena, Montepulciano, Pienza, Cortona, Perugia, and Florence. Each location is a repository of history, art, and culture, radiating its own unique allure.
From the iconic Piazza del Campo in Siena to the Renaissance elegance of Pienza; from Cortona's hilltop vistas to the bustling atmosphere of Perugia, and ultimately to Florence – the epicentre of Renaissance art and architecture.
The walks are relaxed, designed to give you plenty of time to absorb the landscapes, engage with local traditions, and truly live the Italian lifestyle. You'll traverse some of the most scenic cities and towns in Tuscany and Umbria with ample opportunities to uncover hidden treasures, taste regional foods, and relish the breathtaking views.
We take care of all your accommodation needs, ensuring you have a cosy place to unwind after a day of discovery. A comprehensive guide, complete with day-by-day plans and GPS navigation through an easy-to-use app, will be at your fingertips.
We'll also offer local tips to enhance your experience in each town. Should any logistical challenges come up, we're on hand to resolve them, allowing you to concentrate on savouring your vacation.
So, are you ready to exchange your office environment for the ambiance of a charming Italian café, your daily drive for a leisurely walk amidst sunlit vineyards, and your morning alarm for the chimes of an ancient bell tower?
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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Self-guided
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