landscape of Tuscany with vineyards and walking trail during tuscany walking holidays
landscape of Tuscany with vineyards and walking trail during tuscany walking holidays

Walking Holidays in Tuscany and Umbria

Hiking in the green, glorious heart of Italy

Picture cypress-lined hills dotted with farmhouses on the rolling fields that shape the iconic landscape of Val d’Orcia.  Cross the meandering path of of Via Francigena and disappear over the hills towards a distant warm-colored, terracotta-roofed village. The views on our Tuscany hiking tours are unforgettable.


The most scenic section of the Camino to Rome is found here. We call it the heart of the Via Francigena. But you can also traverse the wine paradise of  Chianti  or perhaps wander along the “Via Lauretana Toscana” - an itinerary connecting Siena to Cortona.

Our walking holidays in Tuscany are designed to stay with you. 

Tuscany Umbria pienza door to countryside during a tuscany walking holiday

Mysterious, beautiful, verdant Umbria, has forests and paths to enjoy like a walking meditation, hermitages and hamlets, mountains and fortresses: the St. Francis Walk starts from Tuscany and reaches Assisi to then continue to Rome.

Top Trips

Tuscan Via Francigena


Ethereal Beauty, North to South
hiker on an ancient stone bridge during a tuscany walking holiday

The most scenic part of the route unfolds in Tuscany: from the Tuscan gateway at the Futa Pass, through Pontremoli and then towards Versilia, before reaching Lucchesia, Val d'Elsa, the lands of Siena, and Val d'Orcia – an uninterrupted beauty for the eyes and the heart, and one of the most unforgettable experiences for a Tuscany walking holiday.

Via Francigena, Fidenza to Pontremoli

Via Francigena, Pontremoli to Lucca

Via Francigena, Lucca to Siena

Via Francigena, Siena to Viterbo

In Umbria, on St Francis Way


In the green heart of Italy
scenic mountain panorama on the st francis way

The Way of St. Francis is an itinerary that touches upon the most significant places in the life of Saint Francis, with many of them located in Umbria, the green heart of Italy. Our favorite section? From Assisi to Spoleto: you start in Assisi, the birthplace of Francis, with a powerful energy, and continue to Spoleto through Spello with its flower-adorned streets, the mysterious Hermitage of the Carceri, and landscapes of serene and poetic beauty.

St. Francis Way, Assisi to Spoleto

The iconic beauty of Val d'Orcia


Postcard-like landscapes
the pools of bagno vignoni in summer during a tuscany walking holiday

A journey through the most iconic beauty of Tuscany - the Val d'Orcia is the postcard-perfect landscape that comes to mind when thinking of Tuscany. This journey begins in Montepulciano, the homeland of good wine, and takes us through Pienza, the ideal beauty, the enchantment of Bagno Vignoni, the Abbey of Monte Oliveto Maggiore, and finally, the districts of Siena. An enchanting journey.

Val d'Orcia, Montepulciano to Siena

Highlights

  • Enchanting Landscapes: Discover breathtaking sceneries with rolling hills, vineyards, and medieval villages, a paradise for your love of nature and photography
  • Rich Historical and Cultural Heritage: Experience a journey through history, exploring ancient villages, Romanesque churches, and archaeological sites, perfect for your thirst for culture.
  • Gastronomy and Wines: Savor the local cuisine and renowned wines, combining hiking with authentic gastronomic experiences, a true delight for your palate.
  • Diverse and Accessible Trails: Choose from trails for all levels, from easy to challenging, all well-marked and maintained, for a safe and satisfying walking experience.

Frequently Asked Questions

Is Tuscany difficult to explore?

Tuscany and Umbria offer exciting hiking routes that can accommodate all abilities. Lower-level walks among olive groves, strade bianche (gravel roads), and vineyards are perfect for beginners or those looking for easy strolls during a Tuscany walking holiday. For travelers eager for more exertion, routes such as the Via degli Dei include steep climbs and rougher terrain. We highly suggest that you carefully check each trip page – especially the section “Is this trip for me?” – to better understand the level of difficulty.

What is the best time to embark on a walking trip in Tuscany & Umbria?

Spring (April–June) and autumn (September–October) are the best seasons for these regions, thanks to pleasant weather and fewer crowds. November can still be mild, while summer tends to be very hot and busy, especially in art cities and popular tourist areas.

What kind of landscapes can I expect while hiking in Tuscany and Umbria?

The landscapes vary depending on your chosen itinerary. On the Via Francigena and in the Chianti region, you can expect the classic Tuscan scenery of rolling hills, cypress-lined paths, and gravel roads. Other areas, such as northern Tuscany, feel more rugged and medieval, while Umbria, one of Italy’s greenest regions, offers deep forests and serene countryside trails.

How do I book a walking holiday in Tuscany?

If you’ve found a Tuscany walking holiday or an Umbria hiking tour that matches your travel dreams, you have two options:

  1. Send us an email at info@sloways.eu or call us at (+39) 0552340736. We’ll ask for some basic trip details, such as the number of travelers, preferred departure date, and any special requests.
  2. Use our online calculator on each trip page to receive a provisional price for your chosen tour. If you’re happy with the estimate, send us a request and we’ll confirm hotel availability before finalizing your booking.

Is English commonly spoken in Tuscany and Umbria?

In larger cities and tourist areas, you’ll often find English speakers. However, in rural areas and small villages, it’s less common. Knowing a few basic Italian phrases can help – and when in doubt, gestures and translation apps always work!

What kind of accommodations can I expect along the trails?

We provide charming accommodations in B&Bs, farmhouses, and 3-star hotels, all with private rooms and bathrooms. These stays combine comfort with authenticity, allowing you to fully immerse yourself in the Italian walking experience.

Are tour guides available when hiking in Tuscany & Umbria?

All our Tuscany and Umbria walking holidays are self-guided – meaning no fixed group or guide. Travelers enjoy their own adventures using detailed documentation prepared by our local experts. We take care of the logistics, including booking accommodations and transporting your luggage, so you can walk freely and focus on the journey.

Our trips

Book with SloWays

Say 'yes' to the call to adventure and embark on our self-guided hiking holiday in Tuscany.

We believe hiking tours are the best way to experience Europe and here are just a few reasons why you should book one with SloWays:

 

  • Happy customers: Our walking tours come highly recommended on Feefo, from those who’ve experienced our authentic walking adventures.
  • Vacations experts: We've got over 20 years' experience in creating seamless walking tours across Europe, we'll help you to see the very best of Italy.
  • Sustainable tours: We're proud to be Travelife Certified. and we handcraft every tour with the environment in mind.
  • Comfort first: We offer fully customizable itineraries that combine modern hotel stays with charming, traditional accommodations.

Your walking holiday is just a few clicks away. To get started, please get in touch today.

 

 


Wanderlust Nominee Best Specialist Tour Operator 2025
Wanderlust
Nominee Best Specialist Tour Operator 2023
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Touroperating
S-Cape Countryside Travels srl
Borgo Allegri 16R
50122 Firenze FI
P. IVA 05227330486

 
© 2025 SloWays. All rights reserved.
Touroperating S-Cape Countryside Travels srl Borgo Allegri 16R 50122 Firenze FI, Italy
VAT Nr 05227330486
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