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
Choose your style
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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
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
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
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
Only the best adventures across the world, cherry-picked by our team with an in-depth knowledge of the regions.
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
Explore independently and with confidence while we keep everything running from behind the scenes.
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
We are a team of outdoor specialists equipped with the knowledge and insight to bring you the best hiking experiences.














































