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Walking Holidays in Tuscany and Umbria

Experience the soul of Italy by walking through its scenic vineyards, visiting ancient towns, and indulging in regional treats in both Tuscany and Umbria.

STARTING POINT

Siena

FINISH POINT

Florence

DURATION

10 days / 9 nights

SEASON

From March to November

TECHNICAL LEVEL

FITNESS LEVEL

TOUR TYPE

Travel-And-Hike

PRICE

From 2399€/person

  • 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
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Self-guided

INCLUDED IN PRICE

9 nights in 3-star hotels with breakfast
Digital guidebook with itinerary, route instructions, and practical information
GPS navigation with an easy-to-use app
Tour design and organization
Service and support during your hike
Tourist tax

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?

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Frequently Asked Questions

Of course. We aim to make your decision as easy as possible. Therefore, we crafted several selections targeted at particular groups of hikers – Best for Beginners, Best for Advanced Hikers, Mountain Hikes, Pilgrimages, Classic Treks, etc. 


If you remain unsure and overwhelmed, you can fill out this form or book a call with us, and we can help you directly.

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Samo
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info@hiking-tours.com
+14782496098
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Number of people

2
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Self guided:from 2399/person
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Andrew Luff's profile photo

Andrew Luff

Verified customer

A fantastic 3 day self guided Hut to Hut hike around Triglav National Park in Slovenia. We experienced a full range of weather which made it an unforgettable trip. The organisation and back up support with GPS maps etc was excellent. Hut staff were friendly and very happy to give advice and suggestions on the routes and directions. Would recommend.

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Carly Leonard

Verified customer

My friend and I went with Triglav Tours for a 3 day, 2 night hike this summer and had the most amazing time!! Our guide, Bine, was awesome and had lots of cool facts to share about the area we were hiking. Additionally, my friend and I had not completed such a technical hike before and the guide and other guests were very patient with us and encouraging, ensuring we felt safe the entire time. The overnights were also such a fun way to get to know Bine, the other guests, and other hikers as well. Cannot recommend Triglav tours enough!!!

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Michael White

Verified customer

I arranged a six-day/five-night trip with Hut to Hut Slovenia. It's the first time I've gone with a tour organizer and I can say it went really well. In the past I've arranged huts myself and it is a huge hassle figuring out how to make the bookings, if the bookings actually exist, and what good/viable routes might be. Having this all sort was, at least to me, totally worth it. The routing is via Ride with GPS, which was great. I'd recommend bringing 1:25,000 scale paper maps as a backup, just in case. The huts themselves differ wildly. Some are really rustic with, ahem, interesting toilet facilities. One was accessible by road and thus had showers, a long menu, and even espresso. All will have some sort of food, but you might only have two options for dinner (one with meat, one vegetarian). The cuisine in the Slovenian huts leans strongly to stews and goulashes with minimal fresh vegetables and/or fruit. Certainly good and hearty but pretty much everyone I talked to said the food was better in the Italian and Austrian huts. Some huts are cash only, some take cards (but the card reader might be down). A 1.5 litre bottle of water is about 6 euro, so if you have a beer with dinner and also buy lunch you need to carry about 25-30 euro per day in cash (assuming you have a booking that includes breakfast). Of the six days of hiking, four were ridiculously spectacular, with the highlight being sunrise from Mt Stol. Getting up to the high mountains, though, can be crazy steep, with switchbacks only sparsely used. Descents are similarly tough, and you have to watch every step. For the first time ever I used trekking poles and my knees thank me. Two days were a bit of a slog, but this is probably unavoidable getting up to or down from the high terrain. Would I do something like this again? Yes, absolutely! But next time it will probably be the Dolomites.

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Roman Klymenko

Verified customer

Very beautiful hike. I did not expect that Slovenia is so amazing.

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Birgit Kindler

Verified customer

We had a lovely hike today with our guide Klemen. He personalized the tour on our needs and interests, so that we saw places we wouldn't without his experience. The hike was a little bit slippery after the rain from the last days and it went a lot upwards, but it was totally worth it! Thanks again :)

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Dominik Schrotter's profile photo

Dominik Schrotter

Verified customer

We had a great day with Klemen on this hike, he showed us some lesser known spots/highlights of the southern part of the julian alps with a nice viewpoint at the end. 10/10 would book again

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Self-Guided


On a self-guided tour, you explore a destination independently, following a pre-planned route and itinerary without a guide but with all necessary information and accommodation bookings provided in advance.

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