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  • Monday - Friday9am - 5pm
  • Saturday9am - 1pm
  • SundayClosed
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Walking Holidays in Italy

Some countries have it all. Italy is one of them. From the mountain scenery of the Dolomites and the rolling hills of Tuscany to the colourful villages of Cinque Terre and the ancient streets of Rome, Italy offers an extraordinary variety of walking experiences. Add world-renowned food, rich history and landscapes that seem designed for wandering through, and it's easy to see why Italy remains one of our most popular destinations.

Whether you're looking for a guided walking holiday, a self-guided adventure or a leisurely cultural journey, Italy rewards every step.

✔ Book early and pay less – save £100 per person when you book six months ahead.

Popular walking tours in Italy

Classic
Riviera Cinque Terre

Riviera Cinque Terre

Departure dates

  • 2027:
    • Mar
    • Sep

Explore the stunning Cinque Terre coastal region on a walking holiday. Grade 4 walkers enjoy scenic trails, quaint villages, and exceptional views, while Grade 6 walkers tackle challenging climbs. Both groups savour local culture, explore charming towns, and unwind by the sea.

Grade Moderate/Challenging
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Our holiday walking grades

Moderate

Grade 4

Usually, your walk will take up the whole day at a moderate pace. Terrain will often be hilly and paths generally good. Note that on holidays in mountainous areas, expect some rougher paths. An average walk length is 6 miles but expect this to vary from as little as 3 miles on a sightseeing day and up to 10 miles on a full day dependant on the amount of ascent and decent required.

Search all Moderate, Grade 4 walking holidays

Average daily walks - Distance: 6 miles; Ascent/Descent 500m; Terrain: sometimes hilly and undulating on good paths and tracks; Walking Time: Day walks. 

Please note this is a guide only; you should refer to the specific Holiday Information Sheet for the holiday that you are looking at for detailed day to day itinerary and grading information.

Challenging

Grade 6

Full day walks with appreciable amounts of ascent and descent and longer distances covered.  Whilst you will be mainly on paths, these may be rough, steep, and loose at times. We take the whole day to enjoy some fabulous walks.

Search all Challenging, Grade 6 walking holidays

Average daily walks - Distance: 8 miles; Ascent/Descent 850m; Terrain: sometimes rough, loose or steep sections; Walking Time: 8hrs / Full Day walks. 

Please note this is a guide only; you should refer to the specific Holiday Information Sheet for the holiday that you are looking at for detailed day to day itinerary and grading information.

Landscape
From £1,899
7 Nights
With flights
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Adagio
Sights and Delights of Umbria

Sights and Delights of Umbria

Departure dates

  • 2026:
    • Nov
  • |
  • 2027:
    • Mar
    • Apr
    • Jun
    • Oct

Discover the Green Heart of Italy and immerse yourself in all things Italian in Umbria.

Grade Leisurely
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Our holiday walking grades

Leisurely

Grade 3

We still class this level as leisurely; walks are generally a little longer than level 2, with undulations but over a longer distance. Where sightseeing distances are longer, we take a full day with opportunities to stop, rest and refuel. Generally, itineraries involve easy countryside walking with plenty of breaks.  

Search all Leisurely, Grade 3 walking holidays

Average daily walks - Distance: 4 miles; Ascent/Descent 300m; Terrain: generally good paths and tracks; Walking Time: Half Day or Full Day walks. 

Please note this is a guide only; you should refer to the specific Holiday Information Sheet for the holiday that you are looking at for detailed day to day itinerary and grading information.

Culture
From £1,589
7 Nights
With flights
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Adagio
Artistic Umbria

Artistic Umbria

Departure dates

  • 2027:
    • Apr
    • Jun
    • Oct
    • Nov

A journey through history, art and countryside in Umbria, a hidden gem nestled in the heart of Italy, where scenic walking trails weave through medieval hill towns, olive groves and vineyard covered valleys.

Grade Leisurely
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Our holiday walking grades

Leisurely

Grade 3

We still class this level as leisurely; walks are generally a little longer than level 2, with undulations but over a longer distance. Where sightseeing distances are longer, we take a full day with opportunities to stop, rest and refuel. Generally, itineraries involve easy countryside walking with plenty of breaks.  

Search all Leisurely, Grade 3 walking holidays

Average daily walks - Distance: 4 miles; Ascent/Descent 300m; Terrain: generally good paths and tracks; Walking Time: Half Day or Full Day walks. 

Please note this is a guide only; you should refer to the specific Holiday Information Sheet for the holiday that you are looking at for detailed day to day itinerary and grading information.

Culture
From £2,299
7 Nights
With flights
View Details
Discover
The Sorrento Peninsula - Embracing La Dolce Vita

The Sorrento Peninsula - Embracing La Dolce Vita

Departure dates

  • 2027:
    • Apr
    • Sep

Embrace the 'sweet life' on the blissful Sorrento Peninsula. Sun-kissed walks with carefree indulgent local culture awaits.

Grade Moderate
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Our holiday walking grades

Moderate

Grade 4

Usually, your walk will take up the whole day at a moderate pace. Terrain will often be hilly and paths generally good. Note that on holidays in mountainous areas, expect some rougher paths. An average walk length is 6 miles but expect this to vary from as little as 3 miles on a sightseeing day and up to 10 miles on a full day dependant on the amount of ascent and decent required.

Search all Moderate, Grade 4 walking holidays

Average daily walks - Distance: 6 miles; Ascent/Descent 500m; Terrain: sometimes hilly and undulating on good paths and tracks; Walking Time: Day walks. 

Please note this is a guide only; you should refer to the specific Holiday Information Sheet for the holiday that you are looking at for detailed day to day itinerary and grading information.

Food & Wine
From £2,159
7 Nights
With flights
View Details
Discover
Snowshoeing in the Dolomites from St Zyprian

Snowshoeing in the Dolomites from St Zyprian

Departure dates

  • 2027:
    • Feb

Some skiers spend years dreaming of escaping the pistes and discovering the quieter side of the mountains, yet never quite manage to leave the lifts and crowds behind. The answer, however, is wonderfully simple: ditch the skis, strap on a pair of snowshoes, and walk. Within moments the noise of the resort fades away, replaced by the deep silence of snow-covered forests, sparkling alpine meadows and dramatic limestone peaks. Snowshoeing opens up a completely different winter world.

Grade Moderate
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Our holiday walking grades

Moderate

Grade 5

Trips comprise of day walks with plenty of ups and downs, some steep and rough ground will be encountered at times and walks averaging 7 miles with 650m of ascent / descent. Some holidays will cover longer distances on easier paths, others will be shorter walks but have more demanding ascents and terrain.

Search all Moderate, Grade 5 walking holidays

Average daily walks - Distance: 7 miles; Ascent/Descent 650m; Terrain: generally decent paths and tracks with some steeper sections; Walking Time: Day walks. 

Please note this is a guide only; you should refer to the specific Holiday Information Sheet for the holiday that you are looking at for detailed day to day itinerary and grading information.

Snowshoeing
From £2,199
7 Nights
With flights
View Details
Discover
Italy and Sardinia Spring Time Sailing
  • What's NewWhat's New

Italy and Sardinia Spring Time Sailing

Departure dates

  • 2027:
    • Apr

Sail from Southampton on a relaxed Mediterranean voyage combining scenic cruising with guided walking experiences across Spain, Italy and Portugal. From coastal trails in Cádiz and Cinque Terre to cultural highlights in Rome and Porto, this carefully curated programme blends gentle activity, stunning landscapes and immersive local discovery.

Grade Moderate
Close

Our holiday walking grades

Moderate

Grade 4

Usually, your walk will take up the whole day at a moderate pace. Terrain will often be hilly and paths generally good. Note that on holidays in mountainous areas, expect some rougher paths. An average walk length is 6 miles but expect this to vary from as little as 3 miles on a sightseeing day and up to 10 miles on a full day dependant on the amount of ascent and decent required.

Search all Moderate, Grade 4 walking holidays

Average daily walks - Distance: 6 miles; Ascent/Descent 500m; Terrain: sometimes hilly and undulating on good paths and tracks; Walking Time: Day walks. 

Please note this is a guide only; you should refer to the specific Holiday Information Sheet for the holiday that you are looking at for detailed day to day itinerary and grading information.

Cruise
From £4,199
18 Nights
No-fly Cruise
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Discover
Rome: Exploring the Eternal City
  • What's NewWhat's New

Rome: Exploring the Eternal City

Departure dates

  • 2027:
    • Mar
    • Apr
    • Sep

Explore the delightful Eternal City of Rome in autumn, winter, and spring with all its highlights.

Grade Moderate
Close

Our holiday walking grades

Moderate

Grade 4

Usually, your walk will take up the whole day at a moderate pace. Terrain will often be hilly and paths generally good. Note that on holidays in mountainous areas, expect some rougher paths. An average walk length is 6 miles but expect this to vary from as little as 3 miles on a sightseeing day and up to 10 miles on a full day dependant on the amount of ascent and decent required.

Search all Moderate, Grade 4 walking holidays

Average daily walks - Distance: 6 miles; Ascent/Descent 500m; Terrain: sometimes hilly and undulating on good paths and tracks; Walking Time: Day walks. 

Please note this is a guide only; you should refer to the specific Holiday Information Sheet for the holiday that you are looking at for detailed day to day itinerary and grading information.

Culture
From £2,299
7 Nights
With flights
View Details
See all holidays in Italy

Why walk in Italy with Ramble Worldwide?

Italy is a country best experienced slowly. It's the unexpected café in a village square. The vineyard view you weren't expecting around the next bend. The conversation that starts over lunch and somehow continues until dinner. Walking encourages you to notice these moments.

Beyond the famous landmarks lies a country of hilltop villages, olive groves, mountain trails, family-run restaurants and landscapes that have inspired travellers for generations. Exploring on foot allows you to experience Italy's culture, history and scenery in a way that simply isn't possible from a coach window.

Travelling with Ramble Worldwide means discovering these places alongside experienced leaders who help bring the destination to life, or at your own pace on one of our self-guided holidays.

History brought to life

Italy's history isn't hidden away in museums. It's woven into everyday life.

Roman ruins sit beside modern cafés. Medieval towers overlook bustling piazzas. Ancient pilgrimage routes still guide walkers through landscapes that have changed remarkably little over the centuries.

From Rome and Florence to Venice and Sicily, Italy offers an extraordinary opportunity to experience some of Europe's most important historical and cultural treasures while enjoying rewarding walks and beautiful scenery along the way.

Italy's iconic walking landscapes

One of Italy's greatest strengths is its diversity. The soaring mountains of the Dolomites feel a world away from Tuscany's rolling countryside, while the Mediterranean coast offers a completely different experience again. This variety means there is an Italian walking holiday to suit almost every type of traveller.

When is the best time to visit Italy?

Italy is a year-round destination, although conditions vary between regions.

Spring and autumn are particularly popular for walking holidays, with mild temperatures, colourful landscapes and fewer crowds than the peak summer season. Summer is ideal for higher-altitude destinations such as the Dolomites, while winter offers opportunities to explore cultural cities and southern regions in comfortable conditions.

Whatever the season, Italy rarely struggles to charm its visitors.

Frequently asked questions about walking holidays in Italy

  • When is the best time to go walking in Italy?

    Spring and autumn typically offer the most comfortable walking conditions across much of the country, although destinations such as the Dolomites are particularly popular during summer.

  • Are Italy walking holidays suitable for beginners?

    Yes. We offer holidays across a range of walking grades, from leisurely cultural explorations to more challenging mountain adventures.

  • Can I join an Italy walking holiday as a solo traveller?

    Absolutely. Many of our guests travel solo and enjoy the opportunity to explore alongside a welcoming group of fellow walkers.

  • Do you offer self-guided walking holidays in Italy?

    Yes. Alongside our guided holidays, we offer a range of self-guided adventures that allow you to explore at your own pace while benefiting from carefully planned routes and logistical support.

Discover Italy with Ramble Worldwide

Italy has a way of staying with you. Whether you're exploring the vineyard-covered hills of Tuscany, walking amongst the peaks of the Dolomites, discovering Sicily's volcanic landscapes or wandering through Venice's quieter corners, each region offers its own distinctive charm and character.

Our carefully crafted holidays combine rewarding walks, fascinating culture and memorable experiences, allowing you to experience one of Europe's most captivating destinations at a pace that feels just right.

Ways to explore Italy

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Adagio

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Self-Guided

Self-Guided Collection walks in Italy

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Italy walking holidays inspiration

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