Longer Walking Holidays in Italy: Extended Journeys to Explore More, Step by Step

Some trips allow you to see a place.
Longer walking holidays allow you to truly explore it.

At Sloways, we’ve created a collection of extended multi-day walking tours designed for those who want more time on the trail — whether that means completing an entire pilgrimage route, combining two iconic journeys, or discovering a region in depth across different landscapes.

These itineraries typically last 10 days or more and are built for walkers who enjoy steady rhythm, meaningful distances, and the satisfaction of seeing landscapes gradually unfold.

Here are some of our favourite long walking journeys in Italy.

Discover them all! 

 
The Via Francigena & the Way of St Francis: Two Pilgrimage Routes, One Grand Journey

This extended itinerary connects two of Italy’s most historic pilgrimage routes into one continuous walking experience.

You begin along the Via Francigena, walking through classic Tuscan landscapes of vineyards, cypress-lined roads, medieval towns and rolling countryside. The route then transitions into the Way of St Francis, leading into quieter, forested paths and spiritually significant places linked to Franciscan heritage.

The result is a varied and immersive journey that blends history, nature, and cultural depth across central Italy.

Ideal for those who:

• Want to complete substantial sections of two iconic Italian pilgrimage routes
• Enjoy structured, stage-by-stage walking itineraries
• Are looking for a 2-week journey with strong historical identity

 
Matera & the Salento Coast: From Inland Landscapes to the Sea

This long-distance itinerary connects two strikingly different southern Italian landscapes into one cohesive experience.

The journey begins along the Via della Costa Salentina, where coastal paths overlook dramatic cliffs, hidden coves and crystal-clear waters. Small seaside towns and rural tracks shape the rhythm of the first part of the walk.

The second part leads inland toward Matera, one of Italy’s most extraordinary cities, famous for its ancient cave dwellings (Sassi) and unique rocky landscapes.

Sea and stone, coastline and canyon: this itinerary combines them into one extended southern adventure.

Ideal for those who:

• Want a long walking holiday that blends sea views with cultural discovery
• Enjoy varied terrain and contrasting landscapes
• Are looking for a multi-region itinerary in southern Italy
   

Langhe, Cinque Terre & Florence: Hills, Vineyards and Coastal Trails

This extended itinerary links three distinctive regions into a single multi-day walking journey.

You begin in the Langhe, walking through vineyard-covered hills and quiet rural paths. The landscape then shifts dramatically as you reach the Cinque Terre, where terraced trails connect colourful seaside villages overlooking the Mediterranean.

The final stretch leads toward Florence, adding a Renaissance backdrop to a journey that moves from countryside to coast to historic city.

This is a route designed around contrast and variety, allowing you to experience different Italian identities within one extended holiday.

Ideal for those who:

• Want a long journey connecting multiple iconic regions
• Enjoy alternating between inland trails and coastal paths
• Are looking for a structured but diverse walking experience

 
Grand Tour of Tuscany: Chianti & Val d’Orcia in Depth

For those who prefer to explore one region thoroughly, this extended Tuscan itinerary focuses entirely on depth rather than contrast.

Walking through Chianti and Val d’Orcia, you move between vineyards, olive groves, medieval villages and panoramic countryside. The stages are designed to allow immersion in the landscape without rushing between regions.

This itinerary offers continuity and cohesion — ideal for travellers who want to fully absorb Tuscany’s rhythm and character.

Ideal for those who:

• Prefer exploring one region in depth
• Enjoy classic Tuscan scenery and wine-country landscapes
• Are looking for a well-paced, multi-day walking holiday

 
Via Francigena & Cinque Terre: From Pilgrim Paths to Coastal Trails

This extended itinerary connects two of Italy’s most iconic walking landscapes into one continuous journey.

The first part follows a beautiful stretch of the Via Francigena from Lucca to Siena, walking through rolling Tuscan countryside, vineyards, cypress-lined roads and medieval towns. It’s a classic pilgrimage setting — structured, historic, and deeply rooted in cultural tradition.

From there, the journey shifts toward the Ligurian coast and the Cinque Terre, where dramatic cliffs, terraced hillsides and colourful seaside villages offer a completely different atmosphere. The contrast between inland Tuscany and the Mediterranean coastline gives this itinerary a dynamic and varied character.

It’s a long walking holiday that combines structure and variety, making it ideal for travellers who want both historical depth and spectacular scenery in one extended experience.

Ideal for those who:

• Want to walk part of the Via Francigena but add coastal landscapes
• Enjoy varied terrain within a single long itinerary
• Are looking for a multi-day walking tour that balances culture and sea views

 
Why Choose a Long Walking Tour?

There is a clear difference between a short walking break and a 10+ day walking tour in Italy.

With longer itineraries:

• Your body adapts and finds its rhythm
• You become familiar with the landscape rather than just passing through
• Logistics simplify as the journey flows naturally
• The experience becomes continuous rather than fragmented
  
  

  Long walking journeys are particularly suited to those who:

• Already enjoy multi-day walking
• Have the time to travel more slowly
• Prefer immersion over highlights
  
  And because our trips include carefully selected accommodations and luggage transfer when available, these long walking holidays in Italy remain comfortable and well-paced, even over extended distances.

 
Planning the Right Extended Walking Holiday

When choosing among the best long walking tours in Italy, consider:

• Total duration (10 days? Two weeks? More?)
• Terrain variety (hills, coast, countryside, pilgrimage routes)
• Daily distances and elevation
• Season and climate
• Whether you prefer to explore one region deeply or connect multiple areas
  
  
  Each itinerary has its own character. The key is matching it to your energy, your interests, and the time you have available.

 
Walk Further. Discover More.

Long journeys are not about covering more ground.
They are about giving space to what unfolds along the way.

If you are considering one of our extended walking holidays in Italy, explore the routes above — or contact us to help you choose the long-distance itinerary that fits you best.

The path is already there.
All that remains is deciding how far you would like to go.