Walking Holidays

Showing 201 out of 334 trips

It's time to look forward to your next holiday with Headwater. After a spectacular year of interest-packed, self-guided holidays, 5-star client feedback and award wins, we're still just as excited to be offering brand new and unique hand-crafted walking itineraries as we were all those years ago when we started out.

Travelling on foot is one of the best ways to soak up the sights, sounds and scents of some of the world's most wonderful places. Whether you choose to embark on guided or self-guided walking holidays with Headwater, we can point you in all the right directions so you can discover the heart of each destination. From wandering through the majestic mountains and deep valleys of the Swiss Alps to ambling across the hushed forests and vineyards of the Venetian Hills , you can soak up the most sublime views and enjoy close encounters with the local wildlife. If you prefer walking holidays among cooler climates, Dorset's Jurassic Coast provides an incredible backdrop of dramatic cliffs that jut out above the rugged waters.

So, why not take the opportunity to browse through our collection of self-guided and guided walking trips that are designed to immerse you into the destination's local culture, or find inspiration by reading our blog .

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Malta + Gozo : Malta

Highlights of Secrets of Malta Walking

NZ$1340


4.5 (2 reviews)

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Self-guided walking

4 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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United Kingdom : Devon

The English Riviera & Dart Valley Walk

NZ$1450

 
 

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Self-guided walking

4 nights,
twin centre

Level: 2
Moderate

Printed route
directions

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Malta + Gozo : Gozo

Walking on Glorious Gozo - Short Break

NZ$1450

NEW FOR 2025

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Self-guided walking

4 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

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United Kingdom : The Channel Islands

Walking in Guernsey and Sark

NZ$1475

NEW FOR 2025

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Self-guided walking

3 nights,
single centre

Level: 1+ & 2

Headwater
Navigation App

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United Kingdom : The Channel Islands

Walking in Jersey Premium

NZ$1605

NEW FOR 2025

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Self-guided walking

3 nights,
single centre

Level: 1+ & 2

Headwater
Navigation App

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Slovenia

Lake Bled and Lake Bohinj Walk

NZ$1715


4.5 (20 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1+ & 2

Printed route
directions

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Malta + Gozo

Discovering the Maltese Islands

NZ$1850


4.1 (7 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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Spain : The Canary Islands

Walking the trails of Tenerife

NZ$1935


4.5 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2 & 3

Headwater
Navigation App

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Portugal : The Azores

Walking the Green Island of the Azores

NZ$1980


5.0 (1 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Malta + Gozo : Gozo

Walking on Glorious Gozo

NZ$2025

NEW FOR 2025

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Self-guided walking

7 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

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Spain : Andalucia

Walking in Sierra de Aracena

NZ$2090


4.8 (10 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

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Spain : Asturias

Majestic Mountains of the Picos de Europa

NZ$2180


4.8 (8 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Austria : The Tyrol

Walking the Kitzbühel Alps Trail

NZ$2220

NEW FOR 2025

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

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United Kingdom : Scotland

Walking St Cuthbert's Way

NZ$2245


4.5 (2 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

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Spain : The Canary Islands

Contrasts of Lanzarote

NZ$2290


5.0 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Spain : The Canary Islands

Contrasts of La Gomera

NZ$2310


4.2 (5 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Portugal : Madeira

Walking the Waterways and villages of Madeira

NZ$2310


4.2 (6 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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United Kingdom : Scotland

Walking the Speyside Way

NZ$2330


4.5 (2 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

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Italy : Umbria

Undiscovered Villages of Umbria Walk

NZ$2355


4.8 (11 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Spain : The Canary Islands

Walking on Gran Canaria

NZ$2400


5.0 (7 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : The Bay of Naples

The Islands of Amalfi Walk

NZ$2440


4.6 (12 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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United Kingdom : Scotland

Walking the Rob Roy Way

NZ$2485

 
 

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

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Spain : The Canary Islands

Walking in Fuerteventura along the GR 131

NZ$2510

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Headwater
Navigation App

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United Kingdom : Scotland

Walking the West Highland Way

NZ$2530


4.0 (2 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

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Spain : The Canary Islands

Volcanoes and Vineyards of Lanzarote

NZ$2620


4.4 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 2+

Headwater
Navigation App

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France : The Pyrenees

Basque Country : From the Mountains to the Ocean

NZ$2640

 
 

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Germany : Saxon Switzerland

Walking in the Elbe Sandstone Mountains

NZ$2660

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

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Croatia

Dalmatian Coast Island Hopping

NZ$2705


4.8 (13 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Croatia

Dalmatian Islands Walk

NZ$2795


4.9 (8 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+ & 2

Printed route
directions

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Spain : The Canary Islands

Walking across La Gomera

NZ$2950

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Portugal : The Algarve

Walking Rota Vicentina North Fishermen's Trail

NZ$2950

 
 

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : Normandy

Normandy Walk from Deauville to Bayeux - Deluxe

NZ$3015


5.0 (2 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

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Italy : Italian Lakes

Walking at Lakes Orta and Maggiore

NZ$3255

NEW FOR 2025

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+ & 2

Headwater
Navigation App

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Spain : The Canary Islands

Walking in Tenerife and La Palma

NZ$3540

 
 

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Self-guided walking

7 nights,
twin centre

Level: 3
Stretching

Headwater
Navigation App

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Morocco

Highlights of Morocco - In Comfort

NZ$3850

 
 

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Guided group walking

14 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Spain : The Canary Islands

Contrasts of Tenerife Walk (with transfers)

NZ$4290

 
 

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Self-guided walking

7 nights,
twin centre

Level: 1+ to 2+

Headwater
Navigation App

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Canada : Sunshine Coast

Walk & Paddle Canada's Sunshine Coast

NZ$5960

NEW FOR 2025

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Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 1+ to 3

Headwater
Navigation App

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Norway

Walking Norway's Fjords: Hardangerfjord from Bergen

NZ$6865

NEW FOR 2025

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

VIEW TRIP

Italy : Sicily

Walking the Highlights of Western Sicily

NZ$2420

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : The Bay of Naples

The Amalfi Coast Walk

NZ$4640


4.8 (87 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Sicily

Volcanoes of Sicily Walk

NZ$3210


4.4 (11 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : The Loire

Chateaux Of The Loire Walk

NZ$2990


4.4 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

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France : Corsica

North Corsican Wonders Between Coast and Mountains

NZ$2840


4.0 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Printed route
directions

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Malta + Gozo : Gozo

Walking on Gozo - Calypso's Isle

NZ$1915


4.6 (143 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

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Spain : The Canary Islands

Contrasts of Tenerife Walk (with car hire)

NZ$2795


4.7 (11 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 1+ to 2+

Headwater
Navigation App

VIEW TRIP

Italy : The Bay of Naples

Paths of the Amalfi Coast

NZ$1825


4.6 (28 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : The Bay of Naples

Walking Amalfi's Path of the Gods

NZ$1980


5.0 (2 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : Veneto

Walking in the Venetian Hills

NZ$2400


4.7 (88 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Italy : Puglia

Self Guided Walking in Puglia: From Lecce to Matera

NZ$2575


4.7 (49 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Italy : Tuscany

A Taste of Tuscany Walking

NZ$2795


4.9 (28 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : The Dolomites

Walks in The Italian Dolomites

NZ$2990


4.9 (126 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Bermuda

Islands of Bermuda Walk

NZ$3100


4.6 (35 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Switzerland : The Bernese Oberland

Walking the Bernese Highlights West

NZ$3125


4.0 (1 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 4
Challenging

Navigation App

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Portugal : Madeira

Marvels of Madeira Walk

NZ$3145


4.7 (123 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : Provence

Landscapes of the Luberon Walk

NZ$3235


4.7 (37 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Switzerland : The Bernese Oberland

Walking the Bernese Highlights East

NZ$3410


5.0 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

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Italy : The Dolomites

Walking the Dolomites of Alta Badia

NZ$3475


4.8 (23 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Switzerland : Davos

Walking in Val D'Anniviers

NZ$3630


5.0 (1 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 3

Printed route
directions

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United Kingdom : Northumberland

Walking the Best of Hadrian's Wall

NZ$1520


4.8 (29 reviews)

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Self-guided walking

5 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

United Kingdom : Cornwall

Walking the Lizard Peninsula

NZ$1915


4.0 (2 reviews)

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Self-guided walking

5 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Spain : Catalonia

Catalan Classic Walk

NZ$2180


4.7 (78 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Austria : Salzburg

Walking in Austria's Lake District

NZ$2200


4.8 (18 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

VIEW TRIP

United Kingdom : Cornwall

Walking Cornwall's North coast Padstow to Perranporth

NZ$2245

 
 

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Self-guided walking

5 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Portugal : The Algarve

Walk the Algarve's Wild West

NZ$2330


4.8 (87 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Ireland

Walking the Kerry Way and Killarney N.P.

NZ$2510


4.8 (4 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

Austria : Salzburg

Austrian Lakes Activities

NZ$2575


4.8 (68 reviews)

VIEW TRIP

Multi-activity holiday

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

France : The Dordogne

Dordogne River Walk

NZ$2640


4.7 (29 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

United Kingdom : Wales

Highlights of the Pembrokeshire Coast

NZ$2840


3.9 (8 reviews)

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Self-guided walking

6 nights,
twin centre

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Spain : Andalucia

White Villages of Andalucia Walk

NZ$2860


4.9 (136 reviews)

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Guided group walking

7 nights,
single centre

Level: 1+
Leisurely plus

Printed route
directions

VIEW TRIP

United Kingdom : Lake District

Literary Walking in the Lake District

NZ$3080


4.8 (32 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Switzerland : The Bernese Oberland

Classic Swiss Alps Walk

NZ$3210


4.8 (134 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

United Kingdom : The Cotswolds

Best of the Cotswolds Walk

NZ$3850


4.8 (13 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

Italy : Piedmont

Gastronomic Barolo Walk

NZ$3980


4.9 (91 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Galicia

Walking the Camino de Santiago

NZ$4070


4.6 (43 reviews)

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Self-guided pilgrimage

10 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Spain : Andalucia

Hidden Valleys of Cordoba Walk

NZ$1255


4.8 (52 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Walking the Green Coast of Minho

NZ$1300


4.0 (1 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Malta + Gozo : Gozo

Walking on Gozo - Calypso's Isle - Short Break

NZ$1320


4.8 (9 reviews)

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Self-guided walking

4 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Germany : Bavaria

Short Break in the Altmuhltal Nature Park

NZ$1450


4.0 (1 reviews)

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

United Kingdom : Devon

Walking Devon's Coastal Highlights

NZ$1630


4.0 (1 reviews)

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Catalonia

Catalan Classic Walk - Short Break

NZ$1670


4.7 (7 reviews)

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Cyprus

Walking the Akamas Peninsula

NZ$1670


4.5 (11 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 1 & 2

Headwater
Navigation App

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Portugal : Mainland Portugal

Walking the Mountains, Valleys & Coast of Minho

NZ$1670


5.0 (1 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

VIEW TRIP

Malta + Gozo : Malta

Secrets of Malta Walking

NZ$1740


5.0 (4 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Andorra

Walking the Rugged Pyrenees of Andorra

NZ$1740


4.0 (2 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 4
Challenging

Headwater
Navigation App

VIEW TRIP

Spain : Asturias

Highlights of the Picos de Europa

NZ$1805


4.3 (6 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

Italy : Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

NZ$1805

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

United Kingdom

Walking the Antrim Way

NZ$1825

 
 

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Greece

Walking on Kythnos Island

NZ$1825


5.0 (2 reviews)

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Self-guided walking

6 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Spain : Andalucia

Walking the White Villages of the Alpujarras

NZ$1825


4.5 (6 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Headwater
Navigation App

VIEW TRIP

Italy : Liguria

Walking in the Cinque Terre and Portofino

NZ$1850


4.3 (7 reviews)

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Self-guided walking

6 nights,
single centre

Level: 2
Moderate

Navigation App

VIEW TRIP

United Kingdom : Dorset

Jewels of the Jurassic Coast Walk

NZ$1850


4.3 (3 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Portugal : Madeira

Walk the Garden Island of Madeira

NZ$1870


4.8 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Catalonia

Catalonia Activities

NZ$1890


4.5 (13 reviews)

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Multi-activity holiday

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Cyprus

Contrasts of Cyprus Walking

NZ$1890


4.6 (7 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+ to 2+

Headwater
Navigation App

VIEW TRIP

Ireland

Walking the Kerry Way and Killarney N.P. - Short Break

NZ$1935


4.0 (1 reviews)

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

Romania : Transylvania

Transylvanian Castles Walk

NZ$1935


5.0 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Spain : Balearic Islands

Walking the Coastal Trails of Menorca

NZ$2000


4.6 (60 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Germany : Bavaria

Walking in the Altmuhltal Nature Park

NZ$2000


4.0 (1 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

France : The Loire

Chateaux Of The Loire Walk - Short Break

NZ$2025

 
 

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

VIEW TRIP

United Kingdom : Devon

Contrasts of Devon Walking

NZ$2025


4.7 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Balearic Islands

Walking Mallorca's Mountains and Coast

NZ$2025


3.3 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : Alsace

Villages & Vineyards of Alsace- Short Break

NZ$2070


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Puglia

Undiscovered Puglia Walk - Discovering the South-East Coast

NZ$2070


4.6 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Slovakia

Walking the Tatra Mountains in Slovakia

NZ$2110

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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Austria : The Danube

Walking the Wachau Heritage Trail

NZ$2155


5.0 (2 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Istria

Walking the Highlights of Istria: Italy, Slovenia & Croatia

NZ$2200

NEW FOR 2025

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Spain : The Canary Islands

Walking the Trails of La Palma

NZ$2200


4.3 (8 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

United Kingdom : Devon

Walking South Devon's Coastal Path

NZ$2245


5.0 (1 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : Normandy

Normandy Walk from Deauville to Bayeux

NZ$2245


4.8 (5 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

Greece

Walking on Kythnos Island - Premium

NZ$2265


4.6 (7 reviews)

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : Sardinia

Walking Sardinia's Green Coast

NZ$2265

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : Burgundy

Walking in Burgundy's Vineyards - Short Break

NZ$2290

 
 

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Germany : Bavaria

Walking Bavaria's Lakes and Mountains

NZ$2290


4.7 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

VIEW TRIP

United Kingdom : Wales

North Pembrokeshire Coast Walk

NZ$2310

 
 

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 2+ & 3

Printed route
directions

VIEW TRIP

Germany : Bavaria

Walking the Black Forest to Lake Constance

NZ$2310

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Czechia

Walking through Bohemia

NZ$2310


4.8 (5 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

VIEW TRIP

France : The Loire

Multi Activity in the Loire

NZ$2330

 
 

VIEW TRIP

Multi-activity holiday

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Austria : The Tyrol

Alpine Walks in the Stubai Valley

NZ$2355


4.6 (11 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Austria : The Tyrol

Walking the Tyrolean Mountains

NZ$2400


5.0 (1 reviews)

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Self-guided walking

6 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Andorra

Walk across Andorra

NZ$2400


4.6 (5 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 4
Challenging

Headwater
Navigation App

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United Kingdom : Wales

Highlights of the Gower Peninsula Walk

NZ$2440


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

5 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Austria : Salzburg

Salzkammergut Lakes Walk - Short Stay

NZ$2485

 
 

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

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Italy : Campania

Coastal Cilento Walk

NZ$2485


4.8 (5 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

France : Mont Blanc

Mont Blanc Walks - Short Break

NZ$2530

 
 

VIEW TRIP

Self-guided walking

4 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Switzerland : The Bernese Oberland

Walking in Kandersteg - Short Break

NZ$2530


4.9 (12 reviews)

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Self-guided walking

5 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

United Kingdom

Walking the Western Tip of Cornwall

NZ$2530


4.9 (17 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

VIEW TRIP

United Kingdom : Wales

Walk the Welsh Highland Railway

NZ$2530


3.7 (3 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : The Bay of Naples

Gems of the Amalfi Coast Walking

NZ$2530


4.7 (3 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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Switzerland : Davos

Walk the Crossroads of Five Passes

NZ$2530


4.8 (5 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 3

Headwater
Navigation App

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United Kingdom : The Channel Islands

Walking in Jersey, Guernsey and Sark

NZ$2595


4.4 (14 reviews)

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 1+ & 2

Headwater
Navigation App

VIEW TRIP

Bosnia

Walking the Olympic Mountains of Bosnia

NZ$2620

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Galicia

Highlights of the Camino de Santiago Walk

NZ$2660


4.9 (16 reviews)

VIEW TRIP

Self-guided pilgrimage

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Tuscany

Wine & Walk in Chianti

NZ$2660


4.0 (2 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

United Kingdom : Wales

Walking Offa's Dyke Path (South)

NZ$2660

 
 

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Italy : Umbria

Walking on the Francigena Way

NZ$2685


4.6 (11 reviews)

VIEW TRIP

Self-guided pilgrimage

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Spain : Galicia

Walking across the Pyrenees on the Camino Frances

NZ$2685


4.8 (4 reviews)

VIEW TRIP

Self-guided pilgrimage

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

VIEW TRIP

Spain : The Canary Islands

Highlights of El Hierro Walk

NZ$2705


4.9 (11 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+ & 3

Headwater
Navigation App

VIEW TRIP

France : Burgundy

Walking in Burgundy's Vineyards

NZ$2750


4.7 (6 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

France : Mont Blanc

Mont Blanc Walks - Short Break Premium

NZ$2795

 
 

VIEW TRIP

Self-guided walking

4 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Ireland

Walking and Cycling the Wild Atlantic Way

NZ$2815

 
 

VIEW TRIP

Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

Spain : The Canary Islands

Walking in El Hierro

NZ$2860


4.5 (4 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 1 to 2+

Headwater
Navigation App

VIEW TRIP

Montenegro

Highlights of Southern Montenegro Walk

NZ$2925


5.0 (1 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Walk the Highlights of Northern Portugal

NZ$3015


4.5 (6 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

France : Alsace

Villages & Vineyards of Alsace

NZ$3035


4.4 (7 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : The French Riviera

The French Riviera Golden Islands

NZ$3035

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 1+
Leisurely plus

Printed route
directions

VIEW TRIP

France : The Dordogne

Dordogne Activities

NZ$3060


4.8 (31 reviews)

VIEW TRIP

Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Balearic Islands

Walking Mallorca trails and traditional Fincas

NZ$3100

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

France : The Pyrenees

Walking the Best of the High Pyrenees

NZ$3235


4.7 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Portugal : Mainland Portugal

Portugal Coastal Way to Santiago

NZ$3235


5.0 (6 reviews)

VIEW TRIP

Self-guided pilgrimage

14 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Italy : Piedmont

Walking the Wine Villages of Piedmont

NZ$3300


4.5 (4 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Walking in Gran Canaria and La Palma

NZ$3390

 
 

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 1 to 2+

Headwater
Navigation App

VIEW TRIP

Greece

Walking the Wonders of Crete

NZ$3390

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Wales

Walking Offa's Dyke Path (North)

NZ$3430

 
 

VIEW TRIP

Self-guided walking

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : The Channel Islands

Walking in Jersey, Guernsey and Sark Premium

NZ$3455

 
 

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Switzerland : Valais

Walk in the Home of the Matterhorn

NZ$3455


5.0 (1 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 1 to 3

Headwater
Navigation App

VIEW TRIP

France : Mont Blanc

Walking Tour du Mont Blanc

NZ$3520

 
 

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

Austria : Salzburg

Salzkammergut Lakes Walk

NZ$3610


4.3 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

VIEW TRIP

Norway

Walking in Balestrand

NZ$3630


4.7 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

VIEW TRIP

Cape Verde

Cape Verde's Northern Islands - With Private Guide

NZ$3740


4.8 (5 reviews)

VIEW TRIP

Private guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

VIEW TRIP

France : Mont Blanc

Walking Tour du Mont Blanc - Premium

NZ$3895


4.8 (4 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

United Kingdom : The Cotswolds

The Cotswold Way Walk

NZ$3915


3.7 (3 reviews)

VIEW TRIP

Self-guided walking

9 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Portugal : The Algarve

Walking the Algarve's South West

NZ$3940


4.8 (32 reviews)

VIEW TRIP

Self-guided walking

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Portugal : The Azores

Island Hopping in the Azores

NZ$4290


4.3 (3 reviews)

VIEW TRIP

Self-guided walking

14 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

United Kingdom : Northumberland

Walking from Coast to Coast

NZ$4730


5.0 (1 reviews)

VIEW TRIP

Self-guided walking

17 nights,
hotel-to-hotel

Level: 4
Challenging

Printed route
directions

VIEW TRIP

Norway : Gudbrandsdalen

Guided Walking in Venabu

NZ$4840


4.8 (15 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 2+
Moderate plus

VIEW TRIP

Iceland

Walking Iceland's Diamond Circle

NZ$5060

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

VIEW TRIP

United Kingdom : Wales

Walking Offa's Dyke Path (North to South)

NZ$5370

 
 

VIEW TRIP

Self-guided walking

17 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Canada : Sunshine Coast

Walking Canada's Sunshine Coast

NZ$5610


4.7 (3 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

VIEW TRIP

Japan

Shikoku Pilgrimage Trail

NZ$6885

 
 

VIEW TRIP

Self-guided walking

10 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

VIEW TRIP

China

Walking the Charms of China - With Private Guide

NZ$7370

 
 

VIEW TRIP

Private guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

VIEW TRIP

Japan

Walk the Kumano Kodo

NZ$7390


5.0 (3 reviews)

VIEW TRIP

Self-guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

VIEW TRIP

Japan

Walk the Nakasendo Trail

NZ$7480

 
 

VIEW TRIP

Self-guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

VIEW TRIP

Faroe Islands

Walking the Faroe Islands - With Private Guide

NZ$8120

NEW FOR 2025

VIEW TRIP

Private guided walking

7 nights,
single centre

Level: 2+
Moderate plus

VIEW TRIP

Peru

Walking Machu Picchu - With Private Guide

NZ$9350

NEW FOR 2025

VIEW TRIP

Private guided walking

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

VIEW TRIP

Morocco

Atlas Panorama

NZ$1430

 
 

VIEW TRIP

Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Cyprus

Walking in North Cyprus

NZ$1980


4.0 (1 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Printed route
directions

Operated by
Exodus Travels

VIEW TRIP

Albania

Highlights of Albania

NZ$2640

 
 

VIEW TRIP

Guided group walking

9 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Greece

Mountains & Villages of Evia

NZ$2860


4.8 (4 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 2+
Moderate plus

Printed route
directions

VIEW TRIP

Italy : The Bay of Naples

Walking the Amalfi Coast

NZ$3190


4.7 (10 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Spain : Mallorca

Walking in Mallorca

NZ$3190


5.0 (6 reviews)

VIEW TRIP

Guided group walking

7 nights,
twin centre

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Egypt

Ancient Egypt & Nile Cruise

NZ$3265

 
 

VIEW TRIP

Guided group walking

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

Greece

Walking on the Greek Islands

NZ$3300

 
 

VIEW TRIP

Guided group walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

Italy : Veneto

Walk The Prosecco Hills & Hidden Venice

NZ$3300


4.8 (5 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

VIEW TRIP

France : Mont Blanc

Mont Blanc Highlights

NZ$3400

 
 

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 3
Stretching

Printed route
directions

VIEW TRIP

Italy : Puglia

Walking in Puglia & Matera

NZ$3520


4.3 (12 reviews)

VIEW TRIP

Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Italy : Sardinia

Walking in Sardinia

NZ$3520


5.0 (1 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 3
Stretching

Printed route
directions

VIEW TRIP

Estonia

Discover the Baltics

NZ$3630

 
 

VIEW TRIP

Guided group walking

11 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

France : The French Riviera

Walks & Gardens of the French Riviera

NZ$3850


5.0 (3 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Italy : The Dolomites

Classic Dolomites - Premium

NZ$4400


5.0 (1 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 3
Stretching

Printed route
directions

VIEW TRIP

Portugal : The Azores

Walking in the Azores

NZ$5060

 
 

VIEW TRIP

Guided group walking

7 nights,
twin centre

Level: 3
Stretching

Printed route
directions

VIEW TRIP

Sri Lanka

Walking Trails of Sri Lanka

NZ$5060

 
 

VIEW TRIP

Guided group walking

14 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

VIEW TRIP

Portugal : Mainland Portugal

Portugal: Walking & Wine - Premium Adventure

NZ$5280


4.5 (2 reviews)

VIEW TRIP

Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Peru

The Inca Trail in Comfort

NZ$5720

 
 

VIEW TRIP

Guided group walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

VIEW TRIP

South Africa

South Africa: Walking & Wildlife

NZ$5830

 
 

VIEW TRIP

Guided group walking

14 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

VIEW TRIP

Costa Rica

Discover Costa Rica

NZ$6225

 
 

VIEW TRIP

Guided group walking

14 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

Iceland

Iceland Explorer

NZ$7480

 
 

VIEW TRIP

Guided group walking

9 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Costa Rica

Costa Rica's Coastal Secrets

NZ$8315

 
 

VIEW TRIP

Guided group walking

14 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Nepal

Annapurna Trails & Chitwan - Premium Adventure

NZ$9680

 
 

VIEW TRIP

Guided group walking

12 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

VIEW TRIP

Peru

Peru Explorer

NZ$10340

 
 

VIEW TRIP

Guided group walking

19 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Japan

Japan's Kumano Kodo

NZ$13200

 
 

VIEW TRIP

Guided group walking

13 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

VIEW TRIP

Germany : Bavaria

Walking in Southern Bavaria

NZ$1495


4.7 (52 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 1 & 2

Printed route
directions

VIEW TRIP
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Where appropriate, we grade our holidays based on distance, terrain, elevation gain, remoteness, etc and categorise them into 4 relative groups. This is ultimately subjective and may vary slightly day to day; for more advice, please see the specific trip page or call one of our friendly team.