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Walking Holidays in Tuscany and Umbria

10 days / 9 nights

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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

Season

From March to November

Technical level

2/5

Fitness level

3/5

Tour type

product_attributes.Travel-And-Hike

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Samo Korelec
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  • 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

What’s included in the price?

Self-guided

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

NOT INCLUDED

Tourist tax

OPTIONAL EXTRAS

Hotel upgrades
Luggage transfer
Single supplement
Transfers

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

Our walking holidays in Tuscany are primarily focused on leisurely exploration, offering a delightful experience without significant elevation gain. However, it’s important to note that certain stages of the Via Francigena can be quite long. In addition, we also offer other holiday options that include more demanding hikes. Regardless of the holiday you choose, we aim to provide a high-quality experience catering to different fitness levels. So, whether you prefer leisurely strolls through the picturesque Tuscan countryside or more demanding hikes to push your limits, we have options to suit your preferences and ensure a fulfilling journey.

Absolutely! Our hiking holidays are designed to be inclusive and can be enjoyed by people of various age groups, including children. Most of our tours do not include technically demanding terrain. We believe in the importance of providing opportunities for children to embrace the outdoors and experience the joys of hiking. While a minimum age of eight is recommended to ensure safety and engagement, our tours are generally suitable for individuals who possess basic physical capabilities and can comfortably walk for a few hours daily.

For our walking tours, we highly recommend wearing sturdier hiking shoes that provide ample support, particularly during long hiking days and on uneven terrain. Hiking shoes are designed specifically for outdoor activities, offering features such as sturdy soles, enhanced traction, and ankle support. They are well-suited to handle various terrains, including gravel paths, rocky trails, and uneven surfaces commonly encountered during our walking tours. Opting for appropriate footwear ensures comfort and stability and minimises the risk of foot fatigue or potential injuries.

We highly recommend making an advance booking to ensure accommodation availability. Securing your reservation early increases the likelihood of obtaining your preferred options. If you wait until the start of the season or during the season, availability in hotels and apartments may be limited, and we may not be able to guarantee your desired arrangements.

It’s important to be aware that accommodations at the destinations are in high demand, especially during the summer season. To secure your preferred type of housing, we strongly recommend booking early. By doing so, you increase the likelihood of obtaining the accommodation that best suits your preferences. While the availability of specific lodging options may vary, we assure you that we will make every effort to provide you with the most suitable accommodations based on your preferences. Our team is dedicated to ensuring your stay is comfortable and enjoyable, and we strive to meet your specific requirements to the best of our ability.

Our tours are meticulously planned and designed to be easily navigated by independent travelers. The destinations are well-marked and accessible, allowing you to explore at your own pace. As such, it is unlikely that you will require a guide during your tour.

To ensure you have all the necessary information and guidance, we provide a comprehensive handout that covers essential details about the routes, points of interest, and practical tips. This enables you to enjoy the freedom and flexibility of a self-guided holiday, where you can fully immerse yourself in the experience and discover the beauty of each destination at your leisure.

However, if you prefer to have a guide accompany you during the tours, we are more than happy to accommodate your request. Simply let us know in advance, and we will make the necessary arrangements to provide you with a knowledgeable guide who can enhance your journey with insightful commentary and assistance.

The best time to go on a walking holiday in Tuscany is during the early spring and fall seasons. During these periods, the weather is pleasant, and the crowds are fewer, allowing for a more tranquil and enjoyable experience.

In the early spring, typically from March to May, you can witness the region come alive with vibrant blossoms and lush greenery. The temperatures are mild, making it perfect for exploring the picturesque landscapes of Tuscany on foot. Additionally, the tourist crowds are relatively smaller during this time, providing you with a more intimate and serene setting to immerse yourself in the beauty of the surroundings.

Similarly, the fall season, from September to November, offers a delightful time to visit. The weather remains pleasant, with comfortable temperatures ideal for walking and exploring. The autumn colours add a captivating charm to the landscapes, creating a picturesque backdrop for your walking tour. With fewer visitors compared to the peak summer months, you can fully appreciate the tranquillity and authenticity of the region.

It’s worth noting that the summer months in Tuscany, particularly July, and August, can be quite hot and crowded. While the region maintains its allure during this time, the higher temperatures and increased tourist influx may impact your overall experience. However, if you plan accordingly and take precautions against the heat and the crowds, summer can still offer enjoyable walking opportunities in Tuscany.

In cases of light rain or mild weather disturbances, hiking can often still be safely managed as long as it does not pose any significant risks. The stunning landscapes of Tuscany can take on a unique charm under a drizzle, offering a different perspective and an enchanting experience.

However, in situations where the weather becomes more severe, such as heavy rainstorms or thunderstorms, our team will assess the situation and make appropriate adjustments to ensure your safety. This may involve modifying the planned routes, seeking shelter, or postponing the activity until the weather improves.

Ratings & Reviews

Google Reviews

5.0 average rating

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David Boddy

Verified customer · 21 days ago

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.

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Chris Johnson

Verified customer · about 1 month ago

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.

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Ilma Durmic

Verified customer · 2 months ago

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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Islam Mušić

Verified customer · 3 months ago

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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Aurore Kurc

Verified customer · 3 months ago

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!

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Self-guided

Those who like a good adventure and limitless flexibility should go on a self-guided tour...

HASSLE-FREE

HASSLE-FREE

We handle itineraries, accommodations, and anything else you prefer not to deal with, so you can enjoy a carefree hike.

TRUSTED BY MANY

TRUSTED BY MANY

We are a financially protected company operating since 2014, and with thousands of satisfied customers in the past, we still put you first.

TRIED & TESTED ADVENTURES

TRIED & TESTED ADVENTURES

Only the best walking tours in Tuscany, cherry-picked by our team with an in-depth knowledge of the region.

UNBEATABLE SUPPORT

UNBEATABLE SUPPORT

Our 24/7 customer support is where we show our passion, bringing you a better experience by making your well-being our number one priority.

from 2.399 € /person
Experience the enchanting mediaeval towns, luscious cuisine, and rolling vineyard landscapes with Tuscany Walking Holidays, your gateway to Italian adventures.

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