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Headwater bestsellers - our most popular walking holidays

Walking is one of best ways to travel. You have got time to slow down and drink it all in: the fresh air, the scent of a wildflower on the breeze, the tinkle of a cow bell in the distance. A good walk should be about relaxation, getting away from the stresses of everyday life - and that's exactly the secret to what makes our most popular walking holidays such firm favourites.

There's such a wealth of variety of scenery on offer - with breezy coastal routes, rolling agricultural hills, or dramatic mountainous panoramas, there's no shortage of stunning viewpoints and vistas to discover on foot. We've hunted down the very best of each region to reveal to you what makes them so special, from the perfect places to stay to the hidden gems that make your holiday unforgettable.

Enjoy our selection of favourite walking holidays.


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)
Walking on Gozo - Calypso's Isle
Gozo

Walking on Gozo - Calypso's Isle

Based at the exclusive 5-star Ta Cenc Hotel, the tiny island of Gozo offers secluded beaches, Arabic-style honey-coloured houses, lemon groves, palm trees, red GPO phone boxes and 'Dixon of Dock Green' police stations!

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$1579per person, tour only

  • 102 Reviews
  • All accommodation
  • All buffet breakfasts and evening meals
  • Route notes and maps provided
  • 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)
White Villages of Andalucia Walk
Spain: Andalucia

White Villages of Andalucia Walk

You walk through timeless white washed villages, along flower decked paths - poppies, wild iris, and pink oleander - and there's a good chance of spotting golden eagles soaring overhead.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$2099per person, tour only

  • 104 Reviews
  • All accommodation
  • All meals (including wine at dinner)
  • Led by experienced local guide
  • Flights from London (if booking incl. flights)
Classic Swiss Alps Walk
Switzerland: The Bernese Oberland

Classic Swiss Alps Walk

Here, in the 'jewel in the crown' of classic Switzerland, you'll find many of the highest peaks, the deepest valleys, the tallest waterfalls, the oldest glaciers and the most beautiful mountain lakes in the country.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From Call usper person, tour only

  • 73 Reviews
  • All accommodation
  • All breakfasts, picnic or light restaurant lunches and 4 course evening meals
  • Route notes and maps provided
  • 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)
Marvels of Madeira Walk
Portugal: Madeira

Marvels of Madeira Walk

Perfect for year-round walking, the floating garden of Madeira is a paradise of tropical flowers, exotic birds and trees, romantic gorges and emerald seas. Luxury 4 and 5 star hotels throughout provide exquisite local cuisine with possibility of sampling the island's famous full-bodied wine.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2479per person, tour only

  • 75 Reviews
  • All accommodation
  • All continental breakfasts, 2 picnics and all evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
  • 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)