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1/9

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

Choose your style

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Samo Korelec
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Highlights

  • 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

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

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.

The sooner, the better! Booking in advance ensures you secure a spot, especially on popular routes where accommodations in remote areas can fill up quickly. For tours like the Tour du Mont Blanc and Alta Via, it's best to book several months ahead, as these areas have limited availability in mountain huts.


However, for some of our less-traveled tours, it's possible to book just a few weeks in advance, though availability and comfort may be more limited, particularly in remote areas with fewer options. To ensure you have the best experience, we always recommend booking early, especially during peak hiking seasons.

Our tours offer flexible starting days, allowing you to begin whenever suits you. However, for some of our most popular routes, like the Tour du Mont Blanc (TMB) and Alta Via, we have selected departure days due to high demand and pre-booked accommodations. Be sure to check the specific requirements for these tours.

We offer a variety of tours suitable for different fitness levels and technical abilities. Some of them require no prior hiking experience.


Whether you’re a beginner or an experienced hiker, we have the perfect route for you. You can find more information in our Hiking Difficulty Guide, and we also have dedicated sections for Best for Beginners and Best for Advanced Hikers to help you choose the suitable tour.

The fitness level is based on a scale determined by our hiking experts. It varies depending on the tour and defines the selected hiking tour's physical requirements in comparison to others. For a detailed overview, please refer to our Hiking Difficulty Guide. 

The technical demands of each hike differ. The technical-level scale defines the technical requirements of each tour in comparison to others, ranging from basic walking to scrambling or using specialized equipment. For a more in-depth explanation of the five levels, please refer to our Hiking Difficulty Guide.

Most of our tours are self-guided, meaning you have the freedom to explore at your own pace without being tied to a group schedule. We provide detailed digital guidebooks that include maps, route notes, and GPS files to ensure a smooth experience.


You can learn more about the concept by reading Self-Guided Tours Explained. We include a guide only for the most challenging treks, like the Triglav Summit Climb.

We provide a comprehensive digital guidebook with maps, route notes, accommodation details, and emergency contacts. Our support will be available during the tour. However, you'll have all the information you need to enjoy your hike independently.


Check out how self-guided tours work in more detail and an example of our digital guidebook here.

All available guidance options

Self-guided

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

HANDPICKED ADVENTURES

HANDPICKED ADVENTURES

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VALUE YOUR TIME

VALUE YOUR TIME

With everything on your plate, let us handle the vacation planning, so your valuable time stays exactly where you need it.

SELF-GUIDED TRAVEL

SELF-GUIDED TRAVEL

Explore independently and with confidence while we keep everything running from behind the scenes.

TRUSTED BY MANY

TRUSTED BY MANY

Since 2014, we have taken care of thousands of happy customers, making it our mission to put your satisfaction first.

OUTDOOR SPECIALISTS

OUTDOOR SPECIALISTS

We are a team of outdoor specialists equipped with the knowledge and insight to bring you the best hiking experiences.

from 2.399 € /person
Browse our wide selection of handpicked hiking tours and explore some of the Earth's most pristine, culturally rich, and breathtakingly beautiful landscapes.

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