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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. Few countries are as diverse: it offers mountains, sparkling coastlines, ancient history and sumptuous cuisine. Whether you're strolling through the great art cities of Tuscany and Umbria, admiring the rolling hills and ancient forests of Venetia with their amazing array of beautiful wild flowers, or enjoying the dramatic coastlines of the island of Sicily, you can really get under the skin of the country on Headwater walking holidays in Italy.

We have an array of journeys for all abilities to enjoy, including guided and self-guided options. Browse our walking holidays in Italy below to find gentle coastal trails, scenic walks past the world-famous Barolo, Barbaresco and Moscato vineyards in Piedmont, and high-level walking in northern Italy with the dramatic backdrop of the towering Alps and Dolomites.


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 Barbaresco and Barolo.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3349per person, tour only

  • 75 Reviews
  • All accommodation
  • All continental breakfasts and gastronomic evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Self-Guided Walking in Puglia and Matera
Italy: Puglia

Self-Guided Walking in Puglia and Matera

Independent walking trip allowing you to discover the beauty of Puglia and Matera. Starting in the UNESCO World Heritage site of Matera, you'll make your way south east, through gently rolling countryside filled with olive groves and vineyards, stopping at Alberobello with its 'trulli' houses and the White City of Ostuni before finishing at the heel of Italy in Otranto with a walk along the coastline.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1999per person, tour only
  • All accommodation
  • All breakfasts
  • Route notes and maps 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 typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2099per person, tour only

  • 65 Reviews
  • All accommodation
  • All continental breakfast and evening meals
  • Route notes and maps 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 typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$2249per person, tour only

  • 96 Reviews
  • All accommodation
  • All buffet breakfasts and evening meals
  • Route notes and maps provided
  • 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 typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2279per person, tour only

  • 66 Reviews
  • All accommodation
  • All continental breakfasts and 2 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
  • 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 typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$2349per person, tour only

  • 17 Reviews
  • All accommodation
  • All buffet breakfasts and 4-course evening meals
  • Route notes and maps provided
  • Flights from London (if booking incl. flights)
Amalfi to Sorrento Walk
Italy: The Bay of Naples

Amalfi to Sorrento 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 Amalfi to chic Sorrento, taking in en route vertical Positano and (optional) the beautiful island of Capri.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2649per person, tour only

  • 63 Reviews
  • All accommodation
  • All breakfasts
  • Route notes and maps 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 on our 6 night holiday based in Sestri Levante. Choose each day from the selection of walks available, exploring the coastline along the Cinque Terre. You'll be dazzled by the colours, from the green and blue shades of the sea to the pastel-coloured houses perched above it, to the rich Mediterranean vegetation.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration6 nights, single centre
  • Activity level
  • Excellent for
  • From US$1549per person, tour only
  • All accommodation
  • All breakfasts and 3 dinners
  • Route notes and maps 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. Walking the ancient hillsides studded with lemon groves and framed by deep gorges, we descend from the Agerola Plain to the quaint towns of Positano, Ravello and of course Amalfi itself. No visit to the Bay of Naples would be complete without a trip to see the remains of Pompeii under the imposing volcanic cone of Mount Vesuvius. The best is saved till last with arguably the world's best coastal walk: the 'Walk of the Gods'. Away from the trails, sample incredible food and wine just like the Italians do.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$1649per person, tour only
  • All accommodation
  • All continental breakfasts, 4 picnics and evening meals
  • Route notes and maps provided
  • Flights from London (if booking incl. flights)
A Walk from Spello to Spoleto
Italy: Umbria

A Walk from Spello to Spoleto

This 6-night linear trip is a great mix of wonderfully scenic walking and historic hilltop towns. The walks follow a mix of paths and trails, partly on the St Francis Way, partly on the 'Sentiero degli Ulivi', the Olive Grove Trail. Along the way you pass the great Abbey at Sassovivo and wander the ruins of Campello Alto.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1949per person, tour only

  • 6 Reviews
  • All accommodation
  • All continental breakfasts and 3 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Footsteps of St Francis Walk
Italy: Umbria

Footsteps of St Francis Walk

This 8-night linear trip is a great mix of wonderfully scenic walking and historic hilltop towns. The walks follow a mix of paths and trails, partly on the St Francis Way, partly on the 'Sentiero degli Ulivi', the Olive Grove Trail. Along the way, you explore the upper slopes of the 'bald mountain' Monte Subasio with stunning mountains vistas. You can discover the secluded hermitages of St Francis, pass the great Abbey at Sassovivo and wander the ruins of Campello Alto.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2149per person, tour only

  • 39 Reviews
  • All accommodation
  • All continental breakfasts and 4 evening meals
  • Route notes and maps 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 typeSelf-guided walking
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2279per person, tour only
  • All accommodation
  • All buffet breakfasts and 1 evening meal is included
  • Route notes and maps provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Walking the Olive Trails of Umbria
Italy: Umbria

Walking the Olive Trails of Umbria

This 10-night linear trip is a great mix of wonderfully scenic walking and historic hilltop towns. The walks follow a mix of paths and trails, partly on the St Francis Way, partly on the 'Sentiero degli Ulivi', the Olive Grove Trail. Along the way, you explore the upper slopes of the 'bald mountain' Monte Subasio with stunning mountains vistas. You can discover the secluded hermitages of St Francis, pass the great Abbey at Sassovivo and wander the ruins of Campello Alto.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2349per person, tour only

  • 6 Reviews
  • All accommodation
  • All continental breakfasts and 4 evening meals
  • Route notes and maps 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 typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2579per person, tour only

  • 49 Reviews
  • All accommodation
  • All continental breakfasts and 4 evening meals
  • Route notes and maps 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 holiday! The route takes you through softly rolling hills, sun-drenched hamlets and via the pretty wine towns of Barbaresco and Barolo.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2749per person, tour only
  • All accommodation
  • All continental breakfasts
  • Route notes and maps 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 typeSelf-guided walking
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2849per person, tour only

  • 30 Reviews
  • All accommodation
  • All continental breakfast and 4 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
  • 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 typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$2879per person, tour only

  • 5 Reviews
  • All accommodation
  • 4 nights on Half Board and 3 nights on B&B
  • Route notes and maps provided
  • Flights from London (if booking incl. flights)
Walking the Amalfi Coast
Italy: The Bay of Naples

Walking the Amalfi Coast

The Amalfi Coast is one of the most dramatic coastlines in Europe. Walking the ancient hillsides studded with lemon groves and framed by deep gorges, we descend to the quaint towns of Positano, Ravello and of course Amalfi itself. We visit the remains of Pompeii under the imposing volcanic cone of Mount Vesuvius and also tackle the world's best coastal walk: the 'Walk of the Gods'.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$1399per person, tour only
  • All breakfasts, 4 packed lunches and 6 dinners
  • All accommodation 
  • All transport and listed activities
  • Flights from London (if booking incl. flights)
  • Transfers for group flights
Classic Dolomites - Premium
Italy: The Dolomites

Classic Dolomites - Premium

Guided trekking through the Italian Dolomites. We enjoy an excellent choice of routes with the opportunity to relax in comfort at the end of a day's walking. During the week, we venture into the Fanes-Sennes and Dolomiti di Sesto National Parks for great views of the Tre Cime di Lavaredo.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$1649per person, tour only
  • All breakfasts, 5 lunches, 5 dinners
  • All accommodation (see accommodation section)
  • All transport and listed activities
  • Tour leader throughout
  • Flights from London (if booking incl. flights)
Walks in Puglia and Matera
Italy: Puglia

Walks in Puglia and Matera

This guided walking holiday explores the fascinating region of Puglia taking in the UNESCO towns of Matera and Alberobello and the 'white city' of Ostuni. Walk over rolling hills, through ancient olive groves and past vineyards overlooking the coast.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1649per person, tour only

  • 21 Reviews
  • All breakfasts, 2 dinners and 1 wine and produce tasting 
  • All accommodation
  • Flights from London (if booking incl. flights)
  • Transfers for group flights
Walking in Sardinia
Italy: Sardinia

Walking in Sardinia

A 7-night guided tour exploring Sardinia's stark beauty: crystal clear waters, golden beaches, rocky mountains and undulating limestone ridges. Delicious local cuisine and wines too!

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$1749per person, tour only
  • All breakfasts, 5 picnic lunches, 1 wine tasting and 5 dinners
  • All accommodation (see accommodation section)
  • All transport and listed activities
  • Tour leader throughout
  • Flights from London (if booking incl. flights)
Sicilian Volcanoes
Italy: Sicily

Sicilian Volcanoes

Striking active volcanoes, black beaches, thermal springs and a stunning cobalt sea make the Aeolian Islands a unique must-see destination. Exploring the varied landscape by boat and on foot is without doubt the best way to take in the natural beauty and contrasts of this part of Sicily.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1749per person, tour only
  • All breakfasts, 1 lunch, 1 dinner 
  • All accommodation
  • Flights from London (if booking incl. flights)
  • Transfers for group flights
  • Stromboli summit trek led by volcanologist
Walking the Prosecco Hills
Italy: Veneto

Walking the Prosecco Hills

Based in the heart of the 'Prosecco Road', we spend a week walking through picturesque rolling hills and sampling the area's delicious cuisine and authentic bubbles.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$1749per person, tour only
  • All breakfasts, 4 lunches , 2 dinners and 2 wine tastings included
  • All accommodation
  • London flights (if booking incl. flights)
  • Airport transfers for group flights

    Walking Holidays in Italy

    Overall customer rating, based on 539 reviews

Frequently asked questions

What time of year is best for walking in Italy?

We run our holidays from March through to November though the best time of year for walking in Italy really depends on the sort of season you'd prefer and where you'd like to go in particular. Some regions such as Tuscany are best visited during the summer months whilst Sardinia, being slightly further south, is better suited to the early summer and autumn.

What is included in the price for our Italy walking holidays?

Whilst each package clearly specifies what is included, we do offer, as standard, transport between the Italian airports and the first and last hotel. In addition, all suitcases and baggage are transferred between each hotel and all travel arrangement during the holiday are taken care of by us. Although lunch and evening meals vary depending on your particular holiday, all breakfasts are inclusive.

What abilities are catered for on our walking holidays in Italy:

Our Italian walking holidays have been created to cater for everyone who enjoys walking and has a basic level of fitness. Although no routes have been established that are especially strenuous, we recommend getting in touch if you have any doubts. All of our holidays have an activity rating (Easy, Moderate and Challenging) and you can filter for these if a certain rating doesn't appeal to you.

Will Headwater arrange travel to and from Italy?

Yes. Headwater can arrange this and we offer a variety of options including air and rail travel or even channel crossings if you'd prefer to drive. We can also book flights depending on which regional airport customers wish to travel from.

Is customer service available 24/7 in Italy while on holiday?

Headwater has support staff on hand at all hours and we also have an extensive team on the ground in Italy including all of our associated hotels, our Italian partners and, of course, our exclusive reps. All are on hand to help you if you ever need assistance.