Guided walking in Italy

Here is our range of guided walking holidays in Italy

These guided walking holidays are perfect for people who would like to go walking in Italy with a small group of like-minded people. All our guided walking holidays in Italy are lead by locally based, English-speaking, expert walking guides. We have twin centre and single centre guided walking holidays in the Bay of Naples, Sardinia and Sicily, and hotel-to-hotel guided walking holidays in the Dolomites and on Sicily. In Italy, we also have a wide range of self guided walking holidays to choose from if you'd prefer.

Click on the appropriate 'View Holiday' button for full holiday details, take a look at our activities section for further information about how our guided walking holidays work, or find out more about our activity holidays in Italy.

Walks in Puglia and Matera

Trullo

Please call for prices

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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.

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  • 7 nights, hotel-to-hotel
  • All buffet breakfasts and 1 evening meal
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Great vegetarian meal options.
  • Perfect for couples.
  • Follow stunning coastal routes.

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Contrasts of Sardinia Walk

Cala Fuili Beach, Gulf of Orosei

From $2045 per person

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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.

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  • 7 nights, twin centre
  • All buffet breakfasts, 3 lunches and all evening meals
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Especailly good for solo travellers.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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The Amalfi Coast Walk

Walkers on clifftop path

From $2060 per person

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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.

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  • 7 nights, twin centre
  • All continental breakfasts and evening meals
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Especailly good for solo travellers.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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Tuscany and The Cinque Terre Walk

Cliff view over Vernazza

From $2415 per person

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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.

Departures:
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  • 10 nights, hotel-to-hotel
  • All continental breakfast and 3 evening meals
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Expert-led holidays.
  • Especailly good for solo travellers.
  • Perfect for couples.
  • Follow stunning coastal routes.

View holiday

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Headwater's Guided walking in Italy 4.7245762711864 118
  • ATOL Protected (No. 9957)
  • IATA Registered
  • ABTA Member (No. W1593)
  • Relaxed activity holidays since 1985

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