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

CA$1360


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

CA$1455

 
 

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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

CA$1455

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

CA$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

CA$1590

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

CA$1685


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

CA$1795


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

CA$1875


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

CA$1910


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

CA$1950

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

CA$2005


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

CA$2080


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

CA$2120

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

CA$2140


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

CA$2175


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

CA$200


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

CA$2195


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

CA$2215


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

CA$2235


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

CA$2270


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

CA$2310


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

CA$2350

 
 

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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

CA$2365

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

CA$2385


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

CA$2460


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

CA$2480

 
 

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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

CA$2500

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

CA$2540


4.8 (13 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Croatia

Dalmatian Islands Walk

CA$2615


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

CA$2745

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

CA$2745

 
 

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : Normandy

Normandy Walk from Deauville to Bayeux - Deluxe

CA$2805


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

CA$3015

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

CA$3260

 
 

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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

CA$3325

 
 

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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)

CA$3905

 
 

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Self-guided walking

7 nights,
twin centre

Level: 1+ to 2+

Headwater
Navigation App

VIEW TRIP

Canada : Sunshine Coast

Walk & Paddle Canada's Sunshine Coast

CA$5350

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

CA$6130

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

CA$2290

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

CA$4210


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

CA$2975


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

CA$2785


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

CA$2650


4.0 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Printed route
directions

VIEW TRIP

Malta + Gozo : Gozo

Walking on Gozo - Calypso's Isle

CA$1855


4.6 (143 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Contrasts of Tenerife Walk (with car hire)

CA$2615


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

CA$1780


4.6 (28 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : The Bay of Naples

Walking Amalfi's Path of the Gods

CA$1910


5.0 (2 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Veneto

Walking in the Venetian Hills

CA$2270


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

CA$2425


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

CA$2615


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

CA$2785


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

CA$2880


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

CA$2900


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

CA$2920


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

CA$2995


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

CA$3145


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

CA$3205


4.8 (23 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Switzerland : Davos

Walking in Val D'Anniviers

CA$3335


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

CA$1510


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

CA$1855


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

CA$2080


4.7 (78 reviews)

VIEW TRIP

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

CA$2100


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

CA$2140

 
 

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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

CA$2215


4.8 (87 reviews)

VIEW TRIP

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.

CA$2365


4.8 (4 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

Austria : Salzburg

Austrian Lakes Activities

CA$2425


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

CA$2480


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

CA$2650


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

CA$2670


4.9 (136 reviews)

VIEW TRIP

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

CA$2860


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

CA$2975


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

CA$3525


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

CA$3640


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

CA$3715


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

CA$1285


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

CA$1320


4.0 (1 reviews)

VIEW TRIP

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

CA$1340


4.8 (9 reviews)

VIEW TRIP

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

CA$1455


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

CA$1605


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

CA$1645


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

CA$1645


4.5 (11 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 1 & 2

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Walking the Mountains, Valleys & Coast of Minho

CA$1645


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

CA$1700


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

CA$1700


4.0 (2 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 4
Challenging

Headwater
Navigation App

VIEW TRIP

Spain : Asturias

Highlights of the Picos de Europa

CA$1760


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

CA$1760

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

CA$1780

 
 

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

Greece

Walking on Kythnos Island

CA$1780


5.0 (2 reviews)

VIEW TRIP

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

CA$1780


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

CA$1795


4.3 (7 reviews)

VIEW TRIP

Self-guided walking

6 nights,
single centre

Level: 2
Moderate

Navigation App

VIEW TRIP

United Kingdom : Dorset

Jewels of the Jurassic Coast Walk

CA$1795


4.3 (3 reviews)

VIEW TRIP

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

CA$1815


4.8 (4 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Catalonia

Catalonia Activities

CA$1835


4.5 (13 reviews)

VIEW TRIP

Multi-activity holiday

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Cyprus

Contrasts of Cyprus Walking

CA$1835


4.6 (7 reviews)

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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

CA$1875


4.0 (1 reviews)

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

Romania : Transylvania

Transylvanian Castles Walk

CA$1875


5.0 (7 reviews)

VIEW TRIP

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

CA$1930


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

CA$1930


4.0 (1 reviews)

VIEW TRIP

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

CA$1950

 
 

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

VIEW TRIP

United Kingdom : Devon

Contrasts of Devon Walking

CA$1950


4.7 (3 reviews)

VIEW TRIP

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

CA$1950


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

CA$1985


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Puglia

Undiscovered Puglia Walk - Discovering the South-East Coast

CA$1985


4.6 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Slovakia

Walking the Tatra Mountains in Slovakia

CA$2025

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

CA$2065


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

CA$2100

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

CA$2100


4.3 (8 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

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United Kingdom : Devon

Walking South Devon's Coastal Path

CA$2140


5.0 (1 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : Normandy

Normandy Walk from Deauville to Bayeux

CA$2140


4.8 (5 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

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Greece

Walking on Kythnos Island - Premium

CA$2160


4.6 (7 reviews)

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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

CA$2160

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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France : Burgundy

Walking in Burgundy's Vineyards - Short Break

CA$2175

 
 

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Germany : Bavaria

Walking Bavaria's Lakes and Mountains

CA$2175


4.7 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

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United Kingdom : Wales

North Pembrokeshire Coast Walk

CA$2195

 
 

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Self-guided walking

6 nights,
twin centre

Level: 2+ & 3

Printed route
directions

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Germany : Bavaria

Walking the Black Forest to Lake Constance

CA$2195

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Czechia

Walking through Bohemia

CA$2195


4.8 (5 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

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France : The Loire

Multi Activity in the Loire

CA$2215

 
 

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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

CA$2235


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

CA$2270


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

CA$2270


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

CA$2310


5.0 (2 reviews)

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Self-guided walking

5 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
Navigation App

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Austria : Salzburg

Salzkammergut Lakes Walk - Short Stay

CA$2350

 
 

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

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Italy : Campania

Coastal Cilento Walk

CA$2350


4.8 (5 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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France : Mont Blanc

Mont Blanc Walks - Short Break

CA$2385

 
 

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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

CA$2385


4.9 (12 reviews)

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Self-guided walking

5 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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United Kingdom

Walking the Western Tip of Cornwall

CA$2385


4.9 (17 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

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United Kingdom : Wales

Walk the Welsh Highland Railway

CA$2385


3.7 (3 reviews)

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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

CA$2385


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

CA$2385


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

CA$2445


4.4 (14 reviews)

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Self-guided walking

6 nights,
twin centre

Level: 1+ & 2

Headwater
Navigation App

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Bosnia

Walking the Olympic Mountains of Bosnia

CA$2460

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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Spain : Galicia

Highlights of the Camino de Santiago Walk

CA$2500


4.9 (16 reviews)

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Self-guided pilgrimage

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Tuscany

Wine & Walk in Chianti

CA$2500


4.0 (2 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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United Kingdom : Wales

Walking Offa's Dyke Path (South)

CA$2500

 
 

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : Umbria

Walking on the Francigena Way

CA$2520


4.6 (11 reviews)

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Self-guided pilgrimage

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Spain : Galicia

Walking across the Pyrenees on the Camino Frances

CA$2520


4.8 (4 reviews)

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Self-guided pilgrimage

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

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Spain : The Canary Islands

Highlights of El Hierro Walk

CA$2540


4.9 (11 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+ & 3

Headwater
Navigation App

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France : Burgundy

Walking in Burgundy's Vineyards

CA$2575


4.7 (6 reviews)

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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

CA$2615

 
 

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Self-guided walking

4 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Ireland

Walking and Cycling the Wild Atlantic Way

CA$2635

 
 

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Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Spain : The Canary Islands

Walking in El Hierro

CA$2670


4.5 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 2+

Headwater
Navigation App

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Montenegro

Highlights of Southern Montenegro Walk

CA$2730


5.0 (1 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Portugal : Mainland Portugal

Walk the Highlights of Northern Portugal

CA$2805


4.5 (6 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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France : Alsace

Villages & Vineyards of Alsace

CA$2825


4.4 (7 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : The French Riviera

The French Riviera Golden Islands

CA$2825

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 1+
Leisurely plus

Printed route
directions

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France : The Dordogne

Dordogne Activities

CA$2840


4.8 (31 reviews)

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Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Spain : Balearic Islands

Walking Mallorca trails and traditional Fincas

CA$2880

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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France : The Pyrenees

Walking the Best of the High Pyrenees

CA$2995


4.7 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Portugal : Mainland Portugal

Portugal Coastal Way to Santiago

CA$2995


5.0 (6 reviews)

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Self-guided pilgrimage

14 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Italy : Piedmont

Walking the Wine Villages of Piedmont

CA$3050


4.5 (4 reviews)

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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

CA$3125

 
 

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Self-guided walking

7 nights,
twin centre

Level: 1 to 2+

Headwater
Navigation App

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Greece

Walking the Wonders of Crete

CA$3125

NEW FOR 2025

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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)

CA$3165

 
 

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

CA$3185

 
 

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
Navigation App

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Switzerland : Valais

Walk in the Home of the Matterhorn

CA$3185


5.0 (1 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 3

Headwater
Navigation App

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France : Mont Blanc

Walking Tour du Mont Blanc

CA$3240

 
 

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Self-guided walking

7 nights,
twin centre

Level: 3
Stretching

Headwater
Navigation App

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Austria : Salzburg

Salzkammergut Lakes Walk

CA$3315


4.3 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

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Norway

Walking in Balestrand

CA$3335


4.7 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

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Cape Verde

Cape Verde's Northern Islands - With Private Guide

CA$3430


4.8 (5 reviews)

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Private guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

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France : Mont Blanc

Walking Tour du Mont Blanc - Premium

CA$3565


4.8 (4 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

United Kingdom : The Cotswolds

The Cotswold Way Walk

CA$3585


3.7 (3 reviews)

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Self-guided walking

9 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Portugal : The Algarve

Walking the Algarve's South West

CA$3600


4.8 (32 reviews)

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Portugal : The Azores

Island Hopping in the Azores

CA$3905


4.3 (3 reviews)

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Self-guided walking

14 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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United Kingdom : Northumberland

Walking from Coast to Coast

CA$4285


5.0 (1 reviews)

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Self-guided walking

17 nights,
hotel-to-hotel

Level: 4
Challenging

Printed route
directions

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Norway : Gudbrandsdalen

Guided Walking in Venabu

CA$4380


4.8 (15 reviews)

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Guided group walking

7 nights,
single centre

Level: 2+
Moderate plus

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Iceland

Walking Iceland's Diamond Circle

CA$4570

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

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United Kingdom : Wales

Walking Offa's Dyke Path (North to South)

CA$4835

 
 

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

CA$5045


4.7 (3 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

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Japan

Shikoku Pilgrimage Trail

CA$6150

 
 

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

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China

Walking the Charms of China - With Private Guide

CA$6565

 
 

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Private guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

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Japan

Walk the Kumano Kodo

CA$6585


5.0 (3 reviews)

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

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Japan

Walk the Nakasendo Trail

CA$6660

 
 

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

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Faroe Islands

Walking the Faroe Islands - With Private Guide

CA$7210

NEW FOR 2025

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Private guided walking

7 nights,
single centre

Level: 2+
Moderate plus

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Peru

Walking Machu Picchu - With Private Guide

CA$8275

NEW FOR 2025

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Private guided walking

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

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Morocco

Atlas Panorama

CA$1235

 
 

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Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Cyprus

Walking in North Cyprus

CA$1710


4.0 (1 reviews)

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Guided group walking

7 nights,
single centre

Printed route
directions

Operated by
Exodus Travels

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Albania

Highlights of Albania

CA$2280

 
 

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Guided group walking

9 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Greece

Mountains & Villages of Evia

CA$2470


4.8 (4 reviews)

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Guided group walking

7 nights,
single centre

Level: 2+
Moderate plus

Printed route
directions

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Italy : The Bay of Naples

Walking the Amalfi Coast

CA$2755


4.7 (10 reviews)

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Guided group walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

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Spain : Mallorca

Walking in Mallorca

CA$2755


5.0 (6 reviews)

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Guided group walking

7 nights,
twin centre

Level: 2
Moderate

Printed route
directions

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Egypt

Ancient Egypt & Nile Cruise

CA$2820

 
 

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Guided group walking

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

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Greece

Walking on the Greek Islands

CA$2850

 
 

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Guided group walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

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Italy : Veneto

Walk The Prosecco Hills & Hidden Venice

CA$2850


4.8 (5 reviews)

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Guided group walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

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France : Mont Blanc

Mont Blanc Highlights

CA$2940

 
 

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Guided group walking

7 nights,
single centre

Level: 3
Stretching

Printed route
directions

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Italy : Puglia

Walking in Puglia & Matera

CA$3040


4.3 (12 reviews)

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Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Italy : Sardinia

Walking in Sardinia

CA$3040


5.0 (1 reviews)

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Guided group walking

7 nights,
single centre

Level: 3
Stretching

Printed route
directions

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Estonia

Discover the Baltics

CA$3135

 
 

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Guided group walking

11 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

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France : The French Riviera

Walks & Gardens of the French Riviera

CA$3325


5.0 (3 reviews)

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Guided group walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

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Italy : The Dolomites

Classic Dolomites - Premium

CA$3800


5.0 (1 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 3
Stretching

Printed route
directions

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Portugal : The Azores

Walking in the Azores

CA$4370

 
 

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Guided group walking

7 nights,
twin centre

Level: 3
Stretching

Printed route
directions

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Sri Lanka

Walking Trails of Sri Lanka

CA$4370

 
 

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Guided group walking

14 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

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Portugal : Mainland Portugal

Portugal: Walking & Wine - Premium Adventure

CA$4560


4.5 (2 reviews)

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Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Peru

The Inca Trail in Comfort

CA$4940

 
 

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Guided group walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

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South Africa

South Africa: Walking & Wildlife

CA$5035

 
 

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Guided group walking

14 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

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Costa Rica

Discover Costa Rica

CA$5380

 
 

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Guided group walking

14 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

Iceland

Iceland Explorer

CA$6460

 
 

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Guided group walking

9 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Costa Rica

Costa Rica's Coastal Secrets

CA$7185

 
 

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Guided group walking

14 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Nepal

Annapurna Trails & Chitwan - Premium Adventure

CA$8360

 
 

VIEW TRIP

Guided group walking

12 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

VIEW TRIP

Peru

Peru Explorer

CA$8930

 
 

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Guided group walking

19 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Japan

Japan's Kumano Kodo

CA$11400

 
 

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Guided group walking

13 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

VIEW TRIP

Germany : Bavaria

Walking in Southern Bavaria

CA$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.