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Guided walks in Italy

Whether you've always wanted to witness the dramatic coastlines of the Amalfi Coast, discover the tranquil countryside in Puglia or experience one of the wildest islands in the Mediterranean on a trip to Sardinia, our guided walking holidays in Italy offer something for every adventure seeker.

What areas in Italy do we cover?

Our incredible guided walks in Italy are the ideal choice for those who would like to experience spectacular cities, gorgeous beaches, soaring mountains and stunning scenery - all on foot. With a number of holidays available, it can be difficult to pick one that you think would suit you most. That's where we can help!

Our guided walking holidays in Italy can take you to the Bay of Naples or Sardinia, where we have twin centre and single centre holidays available. If you'd prefer a hotel-to-hotel guided walking holiday, we also have a range of trips available in the Dolomites and Sicily.

At Headwater, our guided walking tours in Italy are perfect for those individuals who are looking to explore the country with a small group of like-minded people. Led by locally-based, English-speaking, expert walking guides, you can rest assured knowing that you are in good hands - and you can ask all the questions you like!

Or perhaps you would like to explore some of these idyllic destinations on your own? If so, we also have a wide range of self-guided walking holidays to choose from. During one of our self-guided trips, you'll be able to dive straight into discovering the magnificent sights, while benefiting from greater flexibility to your schedule.

Allow us to help you plan your next guided walking holiday in Italy

You'll never run out of things to do, delicious dishes to taste and sights to see in Italy. With a flight time of only a couple of hours from the UK, you won't have to travel very far for your next unforgettable trip. Flights can be added as an optional extra.

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

Why not make your own discoveries on one of our carefully-crafted guided walking holidays in Italy? If you're about to plan your next trip and have any questions, one of our experienced team will be able to help.

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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
  • Excellent for
  • From £999per 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
  • Excellent for
  • From £1049per 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
  • Excellent for
  • From £1049per 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
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
  • Excellent for
  • From £1149per 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
  • Excellent for
  • From £1149per 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 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
  • Excellent for
  • From £1199per 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)

    Guided Walking Holidays in Italy

    Overall customer rating, based on 21 reviews