Walking holidays in Italy

There's something very special about Italy. Whether you're a first-time visitor or a seasoned traveller, you'll soon fall under its spell. When you choose walking holidays in Italy with Headwater, you'll get under the skin of this beautiful country. You can stroll the great art cities of Tuscany and Umbria, admire the rolling hills and ancient forests of Venetia, with their stunning array of beautiful wildflowers, or enjoy the dramatic coastlines of Sicily or Sardinia. We have an array of walking journeys for all abilities to enjoy, including guided and self-guided options, helping you tailor your adventure to your preferences.

Browse our walking holidays in Italy below to find gentle coastal trails and scenic walks past the world-famous Barolo, Barbaresco, and Moscato vineyards in Piedmont. Alternatively, you can take on more challenging walking tours in northern Italy with the dramatic backdrop of the towering Dolomites.

Where to go walking in Italy

Here are several of our top Italy walking holiday destinations.

The Amalfi Coast

Renowned for its dramatic coastline, sparkling waters and picture-perfect towns, the Amalfi Coast is a must-visit for those wanting to experience the best of Italy. Head to the charming towns of Positano, Amalfi and Ravello to wander the narrow streets. Immerse yourself in the historic remains of Pompeii and see the iconic Mount Vesuvius. You'll also have the opportunity to walk one of the most famous trails in the world: the Path of the Gods, which offers unrivalled views over the Bay of Naples.

Sardinia

Situated off the west coast of Italy, Sardinia is a large island known for its beautiful beaches, magnificent coastline and spectacular mountains. There are plenty of fantastic hikes to enjoy here, taking you through picturesque gorges with incredible sea views. As you explore Sardinia on foot, you can discover archaeological sites, relax on the beach or go wine tasting at a local vineyard.

Lake Como

Lake Como is a serene destination with endless gems to discover as you skirt your way around the water and beyond. You'll uncover quaint villages and 12th-century abbeys, topped off with unrivalled viewpoints.

Sicily

From volcanic landscapes to dramatic coastlines, Sicily is a haven for anyone wanting to soak up the geographical landforms that make this part of the world so unique. Expect varied routes that take in the imposing Mount Etna and the Aeolian islands.

Italian Dolomites

If you want a walking holiday to Italy that promises a challenge, look no further than the Italian Dolomites. This route allows you to get up close to nature as you tackle striking Alpine terrain. Best suited to experienced walkers, it promises a truly unique experience.

Tuscany

Rolling landscapes, rustic cuisine, and welcoming locals bring the very best of Italy into a walking holiday you won't forget in a hurry. This trip is as much about the food and wine as it is about the walking, all of which you can enjoy against a backdrop of vineyards, olive groves, and freshwater ponds.

 

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The Islands of Amalfi Walk
Italy: The Bay of Naples

The Islands of Amalfi Walk

Sitting prettily in the Bay of Naples lie the beautiful yet diverse islands of Amalfi: Procida, Ischia and Capri. Discover these stunning isles, from Procida's multi coloured harbours, to the thermal spas and terraced vineyards of Ischia and the glamour of Capri's elegant piazze.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07IN
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2060per person, tour only

  • 9 Reviews
  • All accommodation
  • All breakfasts and one evening meal
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Undiscovered Villages of Umbria Walk
Italy: Umbria

Undiscovered Villages of Umbria Walk

This trip combines scenic walking, medieval towns and panoramic hilltop villages, following a mix of quiet country lanes, paths and trails. Along the way, admire the stunning valley vistas from the slopes of Monte Subasio, discover the secluded hermitage of St Francis nestled amongst ancient oak forest.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07UR
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2075per person, tour only
  • NEW FOR 2024  

  • 3 Reviews
  • All accommodation
  • All continental breakfasts
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Secrets of Sicily Walking
Italy: Sicily

Secrets of Sicily Walking

This triple centre holiday explores the unspoilt north western tip of Sicily and the nearby Egadi islands. It's a relatively undiscovered region where highlights include pristine sandy beaches, coral-lined grottoes, ancient hill villages and marvellously preserved nature reserves.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07MR
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2450per person, tour only

  • 96 Reviews
  • All accommodation
  • All continental breakfasts and 2 evening meals
  • Route notes provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
The Amalfi Coast Walk
Italy: The Bay of Naples

The Amalfi Coast Walk

There are few places in Italy as stunning as the Amalfi Coast with its emerald seas, plunging gorges and pastel villages linked by ancient walking paths. This linear walk follows the coast from elegant Ravello to chic Sorrento, taking in en route vertical Positano and (optional) the beautiful island of Capri.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW08AC
  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3980per person, tour only

  • 84 Reviews
  • All accommodation
  • All breakfasts
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Volcanoes of Sicily Walk
Italy: Sicily

Volcanoes of Sicily Walk

Undoubtedly one of the most spectacular, varied and unique walks in our portfolio, taking in the beautiful Aeolian Islands as well as the immense and impressive Mount Etna - the largest active volcano in Europe!

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07AI
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2555per person, tour only

  • 5 Reviews
  • All accommodation
  • All continental breakfasts
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Walking Amalfi's Path of the Gods
Italy: The Bay of Naples

Walking Amalfi's Path of the Gods

Discover some of the highlights of the world renowned Amalfi Coast, along panoramic footpaths lined with terraced vineyards and fragrant lemon groves, connecting Amalfi, Ravello and picture perfect Positano.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07AG
  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$1700per person, tour only
  • NEW FOR 2024  
  • All accommodation
  • All continental breakfasts
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Paths of the Amalfi Coast
Italy: The Bay of Naples

Paths of the Amalfi Coast

The Amalfi Coast is one of the most dramatic coastlines in Europe. Mountains jut steeply out of the Mediterranean and picturesque towns nestled in the coves below. Walk the ancient hillsides studded with lemon groves and framed by deep gorges, from the Agerola Plain to the quaint towns of Positano, Ravello and Amalfi. The best is saved till last with arguably the world's best coastal walk: the 'Walk of the Gods'.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07BO
  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$1805per person, tour only

  • 27 Reviews
  • All accommodation
  • All continental breakfasts, 4 picnics and all evening meals
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Self Guided Walking in Puglia: From Lecce to Matera
Italy: Puglia

Self Guided Walking in Puglia: From Lecce to Matera

Independent walking trip to discover the beauty of Puglia and Matera. Starting in the heel of Italy’s Baroque Lecce, head north through gently rolling countryside filled with olive groves and vineyards. Visit the white city of Ostuni, Alberobello with its iconic 'trulli' houses and the UNESCO World Heritage site of Matera with its unique cave houses.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07PM
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1805per person, tour only

  • 35 Reviews
  • All accommodation
  • All breakfasts
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Walking in the Venetian Hills
Italy: Veneto

Walking in the Venetian Hills

The wonderfully unspoilt Venetian countryside is only an hour or so from the great city of Venice, but couldn't be more different! Here is a landscape of rolling hills, shady forests, vineyards and fields ablaze with colourful flowers.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW08VN
  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2030per person, tour only

  • 84 Reviews
  • All accommodation
  • All continental breakfast and 6 evening meals
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Walks in The Italian Dolomites
Italy: The Dolomites

Walks in The Italian Dolomites

The Italian Dolomites are a Mecca for high-level walkers and this holiday combines superbly varied walking by day with luxury 4 star comfort at night - a highly sought-after mix! Excellent birdspotting, stunning flowers and unrivalled Alpine views.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07DL
  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$2495per person, tour only

  • 120 Reviews
  • All accommodation
  • All buffet breakfasts and evening meals
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
A Taste of Tuscany Walking
Italy: Tuscany

A Taste of Tuscany Walking

Based in the town of Chianciano Terme, on this single-centre walking holiday you’ll experience archetypal Tuscany: stunning timeless landscapes, delicious rustic cuisine, friendly local people and, of course, interesting walking routes.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07ST
  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$2675per person, tour only

  • 27 Reviews
  • All accommodation
  • All breakfasts and 4-course evening meals
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Walking the Dolomites of Alta Badia
Italy: The Dolomites

Walking the Dolomites of Alta Badia

This single centre, self-guided walking week gives easy access to some of the most stunning alpine scenery. Picture postcard villages surrounded by alpine meadows and the jagged limestone mountains of the UNESCO Dolomites.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07DS
  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$2945per person, tour only

  • 20 Reviews
  • All accommodation
  • 4 nights on Half Board and 3 nights on B&B
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Gastronomic Barolo Walk
Italy: Piedmont

Gastronomic Barolo Walk

Superb hotels, world-famous wines and exceptional cuisine are just some of the reasons to choose this 8-night walking holiday! The route takes you through softly rolling hills, sun-drenched hamlets and via the pretty wine towns of La Morra and Barolo.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW08PD
  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3590per person, tour only

  • 91 Reviews
  • All accommodation
  • All continental breakfasts and 4 gastronomic evening meals
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Undiscovered Puglia Walk - Discovering the South-East Coast
Italy: The Bay of Naples

Undiscovered Puglia Walk - Discovering the South-East Coast

Explore Puglia’s pristine coastline, accompanied by glittering sea vistas, fragrant wild flowers and the gentle murmur of ocean waves as you head from Lecce towards Puglia’s most southerly point.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07PL
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1850per person, tour only
  • NEW FOR 2024  

  • 2 Reviews
  • All accommodation
  • All breakfasts
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Coastal Cilento Walk
Italy: Campania

Coastal Cilento Walk

Discover Cilento, a region whose beauty rivals that of the nearby Amalfi Coast,with superb coastal walks, numerous glorious beaches and the ancient site at Paestum.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW08CT
  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1850per person, tour only
  • NEW FOR 2024  

  • 3 Reviews
  • All accommodation
  • All breakfasts and 3 evening meals
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Walking in the Cinque Terre and Portofino
Italy: Liguria

Walking in the Cinque Terre and Portofino

Discover the beautiful Liguria region and its remarkably well-preserved landscape steeped in tradition based in Sestri Levante. Explore the coastline from the Cinque Terre to Portovenere as well as Portofino and the UNESCO island of Palamaria.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW06CT
  • Holiday typeSelf-guided walking
  • Duration6 nights, single centre
  • Activity level
  • Excellent for
  • From US$1895per person, tour only

  • 3 Reviews
  • All accommodation
  • All breakfasts and 6 dinners
  • Route notes provided
  • Flights from London (if booking incl. flights)
Gems of the Amalfi Coast Walking
Italy: The Bay of Naples

Gems of the Amalfi Coast Walking

Stretching 50km from Sorrento to Salerno, the Amalfi Coast is one of the most breath-taking coastlines in Europe. Steep terraces full of scented lemon groves fall sheer into a deep blue Mediterranean sea; whitewashed houses cling precariously to unforgiving slopes while sea and sky merge in one vast blue horizon.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07AM
  • Holiday typeSelf-guided walking
  • Duration7 nights, twin centre
  • Activity level
  • Excellent for
  • From US$2000per person, tour only

  • 2 Reviews
  • All accommodation
  • All breakfasts
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Secrets of Sardinia Walking
Italy: Sardinia

Secrets of Sardinia Walking

A scenic discovery of western Sardinia’s natural beauty and centuries old history, from the black Montiferru mountains to the prolific birdlife of the Sinis wetlands, and from rugged limestone cliffs dotted with panoramic watch towers to the ancient site of Tharros.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07SA
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2120per person, tour only

  • 7 Reviews
  • All accommodation
  • All breakfasts
  • Navigation app provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Wine & Walk in Chianti
Italy: Tuscany

Wine & Walk in Chianti

Walk through the beautiful wine-growing area of Classic Chianti, visiting the World Heritage cities of Florence and Siena.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07TU
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2150per person, tour only
  • All accommodation
  • All breakfasts and 1 evening meal
  • Route notes provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Volterra to San Gimignano Walk
Italy: Tuscany

Volterra to San Gimignano Walk

This 8-night walking holiday combines fabulously unspoilt Chianti countryside with the chance to visit the world-famous cities of Florence and Siena. You'll stay in a mix of friendly, family-run hotels, enjoy superb meals and relax by panoramic pools - views extend as far as Corsica on a clear day!

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW08TY
  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2750per person, tour only

  • 63 Reviews
  • All accommodation
  • All continental breakfasts and 3 evening meals
  • Route notes provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Walking the Wine Villages of Piedmont
Italy: Piedmont

Walking the Wine Villages of Piedmont

Superb hotels, world-famous wines and exceptional cuisine are just some of the reasons to choose this 8-night walking trip! The route takes you through softly rolling hills, sun-drenched hamlets and via the pretty wine towns of La Morra and Barolo.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW08PB
  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2990per person, tour only

  • 3 Reviews
  • All accommodation
  • All continental breakfasts
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Chianti Classic Walk
Italy: Tuscany

Chianti Classic Walk

A 10-night walking holiday that explores the fabulously unspoilt Chianti countryside, with the chance to visit the world-famous cities of Florence and Siena too! Stay in friendly, family-run hotels, including a beautifully restored 12th century abbey, and enjoy superb meals.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW10TY
  • Holiday typeSelf-guided walking
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3050per person, tour only

  • 33 Reviews
  • All accommodation
  • All continental breakfast and 3 evening meals
  • Route notes provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Walking on the Francigena Way
Italy: Umbria

Walking on the Francigena Way

The Francigena Way is an historical journey; a road which once led from Canterbury to Rome and which has been walked by thousands of pilgrims. Your journey will take you from the medieval town of Orvieto, known for its impressive cathedral, through picturesque villages to the grand finale - the 'eternal city' of Rome!

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW09VF
  • Holiday typeSelf-guided walking
  • Duration9 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2105per person, tour only

  • 8 Reviews
  • All accommodation
  • All buffet breakfasts, 1 evening meal and 1 picnic are included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)

    Walking Holidays in Italy

    Overall customer rating, based on 725 reviews

Frequently asked questions

What can I expect from a walking holiday in Italy?

If being out and about in nature or soaking up local culture sounds like the perfect getaway , then a walking holiday tour is the ideal  escape for you. You'll be active for most of the day, so if this suits you, you'll have a brilliant time. The option to choose between a guided or self-guided walking holiday in Italy, as well as a walking grade that matches your ability and preferences, means you can tailor your trip into one that works for you.

Where can I stay in Italy for a walking holiday?

We choose accommodation that oozes charm and offers something a little different, from farm hotels in Tuscany to spa hotels in the Dolomites. We look for friendly hosts who  take a keen interest in their guests, ensuring they get the most out of their stay.

What should I wear for a walking holiday in Italy?

It's important that you pack the right clothing when embarking on a walking holiday in Italy. Having an awareness of what your chosen routes entail will help you get a clear idea of what to pack, and checking the weather is key. We'd recommend that you bring  sturdy walking boots that support your ankles and thick socks are a must.Depending on the season, you might need clothing suitable for hot weather, like shorts and breathable layers. Many opt for a cap that covers their neck, as well as sunglasses. You might need a waterproof jacket with a hood, plus waterproof or lightweight trousers that will dry easily.

What to pack for a walking holiday in Italy?

SPF and sun protection is a given for your walking holiday to Italy, along with protective gear like hats and sunglasses, especially if the weather is due to be hot. Even overcast days can expose you to UV rays so it's important to protect your skin as you'll naturally be spending most of your time outside. Snacks and a water bottle or water pack will mean that you can fuel your body throughout the trip and feel on top form throughout.If you are doing a self-guided walking holiday across some of Italy's trickier terrain especially, you may want to pack a first aid kit.

How are walking holidays in Italy graded?

We give each walking holiday a level so that you can make an informed decision about which option best suits your experience.

  • 1 Boot routes are perfect for anyone seeking a more easy-going trip that less mobile walkers or those with young children can manage.
  • 2 Boot and 3 Boot walking holidays in Italy require greater fitness levels yet are suited to most fit and healthy walkers.
  • 4 Boot tours are ideal for advanced walkers looking for trickier routes to tackle that require training ahead of the trip.

Not sure which level to choose? You can get in touch with our expert team and they will be able to advise you further.

What are the different types of walking holidays in Italy?

As well as considering the level and your desired destination, think about whether you would prefer to do guided or self-guided walks during your holiday in Italy.

Guided walking holidays are ideal if you're looking to socialise during your walks. You'll be placed in a small group and led by a local guide.

Self-guided walking holidays offer different rewards. You'll be able to tackle the route at your own pace using clear instructions on how to get to each point across a designated route.

Why choose a walking holiday in Italy by Headwater?

Providing walking holidays you won't forget in a hurry is what we do best - and Italy is one of our top destinations. Thanks to our secure booking process it means you can commit knowing we have your best interests at heart, as we've been refining our experiences over the past 35 years. So, what are you waiting for? Let us help you find your next adventure.

We're highly regarded - We've been rated 'Excellent' by our customers on Feefo for our personable walking holidays.

Picture-perfect locations - We use a five-step approval process to curate our walking tours, ensuring we include breathtaking destinations and hand-picked hotels with hosts who will make your experience uniquely memorable.

Award-winning walking holidays - We're proud to run award-winning tours. With impeccable customer service and attention to detail, our company has been recognised by the British Travel Awards. 

We can arrange your flights - After providing us with a few details, we can take the reins and arrange flights on your behalf.

Sustainable Travel - Our People, Places & Planet plan reinforces our mission of running our tours as sustainably as possible while working towards becoming Nature Net Positive and reducing our impact on the surrounding environment.

ABTA- and ATOL-protected - You can book with confidence knowing our walking holidays in Italy are ABTA- and ATOL-protected. Find out more about what your key rights are when booking with us.

We aim to empower  communities - Working together with our sister company, Exodus Travels and their Foundation we aim to empower and protect the communities we visit and the environment we explore.

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