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Walking 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 real 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.

View 16 holidays below


The Amalfi Coast Walk

The Amalfi Coast Walk

The Amalfi Coast is renowned for its sensational scenery - the mountains drop into crystal blue seas and the towns cling vertiginously to limestone cliffs. You'll visit stunning Pompeii and stay in elegant Ravello where 'must see' sights include Moorish Vila Rufolo and its semi-tropical gardens.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided walking
  • Duration7 nights, twin centre
  • Activity level
  • Excellent for
  • From £1248

  • 37 Reviews
  • All continental breakfasts and evening meals
  • Led by experienced local guide
Tuscany and The Cinque Terre Walk

Tuscany and The Cinque Terre Walk

Tuscany is packed with cultural and historic interest, hidden art treasures and more antiquarian sites than anywhere else on earth. Explore the great art cities of Florence and Siena, and stroll the stunning Cinque Terre, a UNESCO World Heritage Site favoured by artists and poets.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided walking
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1579

  • 34 Reviews
  • All continental breakfast and 3 evening meals
  • Led by experienced local guide
Walks in Puglia and Matera

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 £899

  • 16 Reviews
  • All buffet breakfasts and 1 evening meal
  • Led by experienced local guide
Walking in the Venetian Hills

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 £919

  • 34 Reviews
  • All continental breakfast and evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
Secrets of Sicily Walking

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 £938

  • 48 Reviews
  • All continental breakfasts and 3 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
Walks in The Italian 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 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 £949

  • 76 Reviews
  • All buffet breakfasts and evening meals included
  • Route notes and maps provided
Connoisseurs' Tuscany Walk

Connoisseurs' Tuscany Walk

A perfect choice for foodies looking for gentle exercise by day and high quality, gourmet accommodation by night! This holiday is based in the unspoilt countryside of the Maremma, with walks possible both inland and on the nearby coast.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £977

  • 43 Reviews
  • All continental breakfasts and evening meals
  • Route notes and maps provided
Footsteps of St. Francis Walk

Footsteps of St. Francis Walk

This 8-night holiday combines relaxed walking through olive groves, sunflower fields and vineyards with time in gorgeous historic towns and sun-drenched villages. Highlights include Etruscan Perugia, picture-postcard Spello, ancient Assisi and the wild Subasio Natural Park.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1099

  • 41 Reviews
  • All continental breakfasts and 6 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
Volterra to San Gimignano Walk

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 £1179

  • 40 Reviews
  • All continental breakfasts and six evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
Undiscovered Tuscany Walk

Undiscovered Tuscany Walk

Tucked away in the most northern corner of Tuscany are the beautiful wooded hills of the Alto Mugello where our walking takes place. Staying in a pretty mountain village, in a tiny 8-room hotel, you'll really get a grass-roots insight into life in the Italian mountains - it's like staying with old friends!

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £1199

  • 24 Reviews
  • All buffet breakfast, 6 picnic lunches and all evening meals
  • Route notes and maps provided
Contrasts of Sardinia Walk

Contrasts of Sardinia Walk

Beyond the sandy beaches and millionaires' yachts, Sardinia offers a land of shepherds' huts, traditional villages and tranquil valleys aching to be explored. On this twin centre holiday, you'll spend 3 nights inland before heading to the coast where you'll enjoy deserted white beaches and colourful fishing ports.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided walking
  • Duration7 nights, twin centre
  • Activity level
  • Excellent for
  • From £1238

  • 39 Reviews
  • All buffet breakfasts, 3 lunches and all evening meals
  • Led by experienced local guide
Amalfi to Sorrento Walk

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 £1329

  • 57 Reviews
  • All buffet breakfasts and 3 evening meals included
  • Route notes and maps provided
  • Luggage transfers between hotels
Chianti Classic Walk

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 £1339

  • 23 Reviews
  • Continental breakfast and 6 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
Islands of Sicily Walk

Islands 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 typeSelf-guided walking
  • Duration9 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1349

  • 33 Reviews
  • All continental breakfasts
  • Route notes and maps provided
  • Luggage transfers between hotels
Exploring the Cinque Terre on foot

Exploring the Cinque Terre on foot

Italy's beautiful Ligurian Coast is both chic and stunning! On this 9-night holiday, you'll visit exclusive Portofino, stay in charming Portovenere and explore the world-famous Cinque Terre, a UNESCO world heritage site, honoured by artists for centuries.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration9 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1399

  • 28 Reviews
  • All buffet breakfast and 4 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
Gastronomic Barolo Walk

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 £1459

  • 46 Reviews
  • All continental breakfast and gastronomic evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels