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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.


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$2179per person, tour only

  • 72 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)
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$3379per person, tour only

  • 64 Reviews
  • All accommodation
  • All breakfasts
  • Route notes and maps provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Walking on Gozo - Calypso's Isle
Gozo / Malta

Walking on Gozo - Calypso's Isle

Based at the exclusive 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$1799per person, tour only

  • 109 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$1849per person, tour only

  • 68 Reviews
  • All accommodation
  • All continental breakfast and 6 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
  • 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$2479per person, tour only

  • 96 Reviews
  • All accommodation
  • All buffet breakfasts and evening meals
  • Headwater navigation provided
  • 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$2499per person, tour only

  • 82 Reviews
  • All accommodation
  • All continental breakfasts, 2 picnics and 5 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Walking the Best of Hadrian's Wall
United Kingdom: Northumberland

Walking the Best of Hadrian's Wall

This walk along Hadrian's Wall, from West to East, starts at Lanercost Priory and ends in Corbridge, taking in some of the best-preserved Roman sites in the UK. The route also passes the world-famous Sycamore Gap as well as some fabulous rolling Northumberland countryside and craggy hillsides, such as those of Walltown, Winshield and Sewingshields Crags.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration5 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From Call usper person, tour only

  • 10 Reviews
  • All accommodation
  • All breakfasts
  • Route notes and maps provided
  • Luggage transfers between hotels
Walking the Lizard Peninsula
United Kingdom: Cornwall

Walking the Lizard Peninsula

A 5 night self guided walking holiday taking in the famed cobbled causeway of St Michael's Mount to the wild serpentine cliffs of Lizard, this is an invigorating and unforgettable walk. Experience the the culinary delights of Porthleven, the magnificent views of Mullion and Kynance and the booming fog horn of Lizard lighthouse.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration5 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1579per person, tour only

  • 6 Reviews
  • All accommodation
  • Breakfasts daily
  • Route notes and maps provided
  • Luggage transfers between hotels
Highlights of the Pembrokeshire Coast
United Kingdom

Highlights of the Pembrokeshire Coast

This twin centre walking holiday incorporates some of the best walking on both the northern and southern sections of the Pembrokeshire Coastal Path. Stay in pretty St David’s, Britain’s smallest city and discover its immaculate beaches, tranquil harbour villages and rugged cliffs,. Then head to Tenby for superb walks with extensive sea views, passing Norman castles, towering sea stacks and unspoilt bays.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration6 nights, twin centre
  • Activity level
  • Excellent for
  • From US$1749per person, tour only
  • All accommodation
  • All breakfasts
  • Route notes and maps provided
  • Luggage transfers between hotels
Walking Cornwall’s North coast Padstow to Perranporth
United Kingdom: Cornwall

Walking Cornwall’s North coast Padstow to Perranporth

A 5 night self guided walk along the Northern Cornish coastline, explore this magnificent coast between two of Cornwall's most famous summer get-aways, Padstow and Perranporth, spending 3 nights in pretty Padstow and 2 nights in popular Newquay. From headland to cove and on to golden sands, the scenery changes as fast as the weather. The shorter daily distances give plenty of time soak up the views and the wild rocky coastline has to be seen to be believed. Bedruthan Steps and Holywell Bay, Newquay town beaches all add their atmosphere and charm to this great walk.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration5 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1799per person, tour only
  • All accommodation
  • Breakfasts daily
  • Route notes and maps provided
  • Luggage transfers between hotels
Literary Walking in the Lake District
United Kingdom: Lake District

Literary Walking in the Lake District

The Lake District National Park is England's most visited national park and this 6 night self-guided walking holiday takes in some of the highlights. Whether you're visiting the home of William Wordsworth while nibbling famous Grasmere gingerbread, surveying Lake Windermere from the top of Latterbarrow Fell, or following the Cumbria Way through beautiful country estates owned by the National Trust, you'll be sure to enjoy an authentic Lakeland experience!

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1979per person, tour only

  • 26 Reviews
  • All accommodation
  • All breakfasts and 1 evening meal
  • Route notes and maps provided
  • Luggage transfers between hotels
Catalan Classic Walk
Spain: Catalonia

Catalan Classic Walk

Beautiful circular walk in Catalonia taking in lovely coastal stretches and unspoilt country landscapes. Fabulous bird and plant life; very good hotels and swimming opportunities every day. Two nights are spent in a luxury castle.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2049per person, tour only

  • 56 Reviews
  • All accommodation
  • All continental breakfast and 2 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Best of the Cotswolds Walk
United Kingdom: The Cotswolds

Best of the Cotswolds Walk

Walk through some of the finest North Cotswold villages with shorter walking days allowing you the maximum time needed to explore the villages and walk at a relaxed pace. Visit beautiful villages including Guiting Power, Broadway and Chipping Campden as well as places of historical interest and some spectacular gardens.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2149per person, tour only

  • 6 Reviews
  • All accommodation
  • Breakfast daily
  • Route notes and maps provided
  • Luggage transfers between hotels
Walk the Algarve's Wild West
Portugal: The Algarve

Walk the Algarve's Wild West

A warming winter walking discovery allowing you to see the best of the unspoilt Western Algarve region. The lush flora and diverse fauna of the Algarvian hinterland compliment the dramatic seascape scenery of the Atlantic coastline perfectly. The hotels are a brilliant mix of rustic charm and stylish grandeur, complete with swimming pools and serving the best of local Portuguese cuisine.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2149per person, tour only

  • 72 Reviews
  • All accommodation
  • All continental breakfasts and 3 evening meals
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Walking in Austria's Lake District
Austria: Salzburg

Walking in Austria's Lake District

A glorious mix of spectacular scenic views, wooded forest trails and picture-perfect 'chocolate box' villages await as you pass crystal-clear lakes, babbling streams and secluded bays.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$2199per person, tour only

  • 7 Reviews
  • All accommodation
  • All continental breakfasts and 1 evening meal
  • Route notes and maps provided
  • 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 US$2199per person, tour only

  • 75 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)
Walking the Kerry Way and Killarney N.P.
Ireland

Walking the Kerry Way and Killarney N.P.

The Kerry Way is the Emerald Isle's longest trail - at 210km, it offers fantastic views of the unspoilt landscapes - a walk here will swathe you in 10,000 years of dramatic Celtic history. Admire crisp blue lakes, pretty waterfalls, lovely little villages and velvety green pastures.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2199per person, tour only
  • All accommodation
  • All breakfasts
  • Route notes and maps provided
  • Luggage transfers between hotels
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$2449per person, tour only

  • 107 Reviews
  • All accommodation
  • All meals
  • Led by experienced local guide
  • Flights from London (if booking incl. flights)
Dordogne River Walk
France: The Dordogne

Dordogne River Walk

This walking holiday explores the limestone cliffs, wooded valleys and beautiful medieval villages that are so unique to France's Dordogne region. World famous prehistoric sites and fine local wines add a further dimension to a stay here.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2849per person, tour only

  • 22 Reviews
  • All accommodation
  • All continental breakfasts and 5 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
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 La Morra and Barolo.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3249per person, tour only

  • 75 Reviews
  • All accommodation
  • All continental breakfasts and 4 gastronomic evening meals
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Walking the Camino de Santiago
Spain: Galicia

Walking the Camino de Santiago

This is one of Europe's classic walks following one of the most ancient pilgrimage routes in the world! There's a real sense of camaraderie and achievement as you chat to fellow walkers from all parts of the globe.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3379per person, tour only

  • 34 Reviews
  • All accommodation
  • All continental breakfast and 7 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)