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Walking holidays in Italy

There's something very special about Italy; whether you're a first time visitor or 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, or 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 a Headwater walking holiday in Italy.

We have an array of journeys for all abilities to enjoy - from gentle coastal trails to scenic walking past the world-famous Barolo, Barbaresco and Moscato vineyards in Piedmont, and for the more experienced we offer high-level walking in northern Italy, with the dramatic backdrop of the towering Dolomites and the Alps.


Paths of the Amalfi Coast
Italy: The Bay of Naples

Paths of the Amalfi Coast

This 7-night guided trip explores the stunning Amalfi Coast, one of the most dramatic coastlines in Europe. 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. Not forgetting a day in the Bay of Naples, where we visit the remains of Pompeii.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £879per person, tour only
  • All breakfasts, 4 lunches and 6 evening meals
  • Led by experienced local guide
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 £969per person, tour only
  • All continental breakfasts, 1 lunch and 1 evening meal
  • Led by experienced local guide
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 £999per person, tour only

  • 52 Reviews
  • All continental breakfast and evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
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 £1049per person, tour only

  • 21 Reviews
  • All buffet breakfasts and 1 evening meal
  • Led by experienced local guide
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 £1059per person, tour only

  • 4 Reviews
  • All continental breakfasts and 5 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
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 **** comfort at night - a highly sought-after mix! Excellent bird-spotting, stunning flowers and unrivalled Alpine views.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £1079per person, tour only

  • 84 Reviews
  • All buffet breakfasts and evening meals
  • Route notes and maps provided
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 £1129per person, tour only
  • All continental breakfasts, 4 lunches, 2 dinners and 2 wine-tastings
  • Led by experienced local guide
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 £1139per person, tour only

  • 9 Reviews
  • All buffet breakfasts and 4-course evening meals
  • Route notes and maps provided
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 £1189per person, tour only

  • 35 Reviews
  • All continental breakfasts and 6 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
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 £1269per person, tour only

  • 58 Reviews
  • All continental breakfasts and 2 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
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 £1299per person, tour only

  • 45 Reviews
  • All continental breakfasts and 6 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
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 £1309per person, tour only
  • All continental breakfasts and 6 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
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 C12 abbey, and enjoy superb meals.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1459per person, tour only

  • 27 Reviews
  • All continental breakfast and 6 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
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 £1529per person, tour only

  • 56 Reviews
  • All breakfasts
  • Route notes and maps provided
  • Luggage transfers between hotels
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 £1649per person, tour only

  • 62 Reviews
  • All continental breakfast and gastronomic evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
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 £969per person, tour only
  • All breakfasts, 5 picnic lunches, 5 evening meals and 1 wine-tasting
  • Led by experienced local guide

    Walking holidays in Italy

    Overall customer rating, based on 456 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.