Holidays with the Headwater Navigation App

Showing 166 out of 305 trips

We offer GPS route navigation on many of our walking and cycling holidays so even if you have no map reading skills - you won't get lost with Headwater!

The Headwater Navigation App provides our comprehensively researched and carefully checked routes in an easy to use and convenient format, with easy-to-follow turn-by-turn instructions all along your route.

Listed below are the holidays that feature the app, to view any of the holidays shown simply click on the 'View holiday' button. To refine your search use the panel above to select the activity type, country, departure months, etc.

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United Kingdom : The Channel Islands

Walking in Guernsey and Sark

NZ$1145

NEW FOR 2026

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Self-guided walking

3 nights,
single centre

Level: 1+ & 2

Headwater
Navigation App

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Malta + Gozo : Malta

Walking on Glorious Gozo - Short Break

NZ$1230


5.0 (3 reviews)

VIEW TRIP

Self-guided walking

4 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Malta + Gozo

Highlights of Secrets of Malta Walking

NZ$1300


4.5 (2 reviews)

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Self-guided walking

4 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Slovenia

Walking in the Soča and Bohinj Valleys

NZ$1385

 
 

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Malta + Gozo : Malta

Walking on Glorious Gozo

NZ$1605


4.5 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : The Channel Islands

Walking in Jersey Premium

NZ$1650

NEW FOR 2026

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Self-guided walking

3 nights,
single centre

Level: 1+ & 2

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Walk the Bonita Island of La Palma

NZ$1760

NEW FOR 2026

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Self-guided walking

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

VIEW TRIP

Malta + Gozo

Discovering the Maltese Islands

NZ$1780


4.4 (12 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Slovenia

Lake Bled and Lake Bohinj Walk

NZ$1805


4.7 (32 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 Lanzarote

NZ$2025


5.0 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Walking the trails of Tenerife

NZ$2110


4.6 (5 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2 & 3

Headwater
Navigation App

VIEW TRIP

Spain : Andalucia

Walking in Sierra de Aracena

NZ$2180


4.8 (16 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Portugal : The Azores

Walking the Green Island of the Azores

NZ$2265


5.0 (3 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Walking in Fuerteventura along the GR 131

NZ$2265


4.7 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Headwater
Navigation App

VIEW TRIP

Italy : Puglia

Cycling the Heel of Italy - Alberobello to Lecce

NZ$2290


4.7 (44 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Denmark

Cycling from Copenhagen

NZ$2375


5.0 (1 reviews)

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Self-guided cycling

4 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Portugal : Madeira

Walking the Waterways and villages of Madeira

NZ$2375


4.2 (6 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Italy : Umbria

Undiscovered Villages of Umbria Walk

NZ$2375


4.7 (16 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Germany : Saxon Switzerland

Walking in the Elbe Sandstone Mountains

NZ$2420

NEW FOR 2026

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

VIEW TRIP

Spain : The Canary Islands

Contrasts of La Gomera

NZ$2440


4.2 (5 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Puglia

Journey through Puglia to Matera

NZ$2485


4.8 (15 reviews)

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Cultural tour

7 nights,
hotel-to-hotel

Headwater
Navigation App

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Spain : The Canary Islands

Walking on Gran Canaria

NZ$2485


5.0 (7 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Volcanoes and Vineyards of Lanzarote

NZ$2510


4.4 (8 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 2+

Headwater
Navigation App

VIEW TRIP

Italy

The Wine Trails of Umbria Cycling

NZ$2530


5.0 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Albania

E-bike Across Southern Albania

NZ$2620


4.9 (7 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Portugal : The Algarve

Walking Rota Vicentina North Fishermen's Trail

NZ$2660


4.5 (2 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : The Bay of Naples

The Islands of Amalfi Walk

NZ$2685


4.6 (14 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Walking across La Gomera

NZ$2685

NEW FOR 2026

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

France : The Pyrenees

Basque Country : From the Mountains to the Ocean

NZ$2705


4.5 (2 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2 & 2+

Headwater
Navigation App

VIEW TRIP

Croatia

Dalmatian Coast Island Hopping

NZ$2815


4.8 (20 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

NZ$2950


4.9 (9 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Greece : Peloponnese

Cycling in the Peloponnese

NZ$3255


4.8 (12 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

United Kingdom : The Channel Islands

Cycling in Jersey, Guernsey and Sark

NZ$3365


4.0 (1 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Italy / Switzerland

Walking at Lakes Orta and Maggiore

NZ$3455


4.9 (7 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Cycling in the Douro Valley

NZ$3500

 
 

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

Italy : Puglia

Cycling the Heel of Italy - Matera to Lecce

NZ$3610


4.7 (14 reviews)

VIEW TRIP

Self-guided cycling

11 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Contrasts of Tenerife Walk (with transfers)

NZ$4335

 
 

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Self-guided walking

7 nights,
twin centre

Level: 1+ to 2+

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Coimbra to Lisbon Cycling

NZ$4510

 
 

VIEW TRIP

Self-guided cycling

11 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Canada : Sunshine Coast

Walk & Paddle Canada's Sunshine Coast

NZ$6775

 
 

VIEW TRIP

Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 1+ to 3

Headwater
Navigation App

VIEW TRIP

Italy : Sicily

Walking the Highlights of Western Sicily

NZ$2550


4.5 (104 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : The Bay of Naples

The Amalfi Coast Walk

NZ$5060


4.8 (93 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Sicily

Volcanoes of Sicily Walk

NZ$3300


4.4 (12 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Malta + Gozo

Walking on Gozo - Calypso's Isle

NZ$1915


4.6 (143 reviews)

VIEW TRIP

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)

NZ$2860


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

Walking Amalfi's Path of the Gods

NZ$1980


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : The Bay of Naples

Paths of the Amalfi Coast

NZ$1980


4.6 (28 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Veneto

Heart of Veneto Cycling

NZ$2355


4.8 (73 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Italy : Puglia

Self Guided Walking in Puglia: From Lecce to Matera

NZ$2440


4.7 (65 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Italy : Veneto

Walking in the Venetian Hills

NZ$2530


4.7 (91 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Italy : Tuscany

A Taste of Tuscany Walking

NZ$2795


4.9 (31 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Sicily

Secrets of Sicily Cycling

NZ$2815


4.6 (25 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Italy : The Dolomites

Walks in The Italian Dolomites

NZ$2815


4.9 (136 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Italy : Tuscany

A Taste of Tuscany Cycling

NZ$2905


4.9 (29 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Portugal : The Algarve

Cycling in The Real Algarve

NZ$3080


4.7 (66 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Bermuda

Islands of Bermuda Walk

NZ$3100


4.6 (39 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Portugal : Madeira

Marvels of Madeira Walk

NZ$3235


4.7 (129 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : The Dolomites

Walking the Dolomites of Alta Badia

NZ$3500


4.8 (28 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Italy : Sicily

Cycling through Baroque Sicily

NZ$3720


4.5 (23 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Switzerland : Valais

Walking in Val D'Anniviers

NZ$3760


4.5 (2 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 1 to 3

Headwater
Navigation App

VIEW TRIP

Slovenia / Italy

Julian Alps to the Adriatic Cycling

NZ$4905


4.8 (128 reviews)

VIEW TRIP

Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Northumberland

Walking the Best of Hadrian's Wall

NZ$1630


4.8 (31 reviews)

VIEW TRIP

Self-guided walking

5 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Germany : Bavaria

Walking in Southern Bavaria

NZ$1740


4.7 (59 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 1 & 2

Headwater
Navigation App

VIEW TRIP

Spain : Catalonia

Catalan Classic Walk

NZ$2485


4.7 (79 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Lake District

Literary Walking in the Lake District

NZ$2485


4.8 (37 reviews)

VIEW TRIP

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$2530


4.8 (156 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : The Dordogne

Dordogne Valleys & Villages Cycling

NZ$2575


4.7 (52 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Portugal : The Algarve

Walk the Algarve's Wild West

NZ$2575


4.8 (90 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

France : The Dordogne

Dordogne River Walk

NZ$2750


4.7 (32 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Balearic Islands

Cycling in Mallorca: Coast to Coast

NZ$2860


4.7 (35 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Austria : Salzburg

Austrian Lakes Activities

NZ$2990


4.8 (69 reviews)

VIEW TRIP

Multi-activity holiday

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Spain : Catalonia

Contrasts of Catalunya Cycling

NZ$3125


4.7 (56 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Italy : Puglia

Contrasts of Puglia Cycling

NZ$3190


4.6 (126 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Spain : Andalucia

Cycling in Andalucia: Seville to Cadiz

NZ$3300


4.4 (17 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

Austria / Germany / Switzerland

Lake Constance Cycling

NZ$3320


4.7 (95 reviews)

VIEW TRIP

Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Croatia

Coastal Croatia - Porec to Pula Cycling

NZ$3365


4.7 (87 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Porto Coastal Cycling

NZ$3610


4.4 (59 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

United Kingdom : The Cotswolds

Best of the Cotswolds Walk

NZ$4070


4.7 (15 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

Italy : Piedmont

Gastronomic Barolo Walk

NZ$4180


4.9 (97 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Piedmont

Gastronomic Barolo Cycling by e-bike

NZ$4820


4.8 (89 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Andalucia

Hidden Valleys of Cordoba Walk

NZ$1275


4.8 (55 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

United Kingdom : Devon

Walking Devon's Coastal Highlights

NZ$1300


4.0 (1 reviews)

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Malta + Gozo : Malta

Walking on Gozo - Calypso's Isle - Short Break

NZ$1320


4.7 (10 reviews)

VIEW TRIP

Self-guided walking

4 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Spain : Catalonia

Catalan Classic Walk - Short Break

NZ$1495


4.7 (7 reviews)

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Malta + Gozo : Malta

Secrets of Malta Walking

NZ$1670


5.0 (4 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Cyprus

Walking the Akamas Peninsula

NZ$1740


4.5 (12 reviews)

VIEW TRIP

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

NZ$1740


5.0 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

France : Alsace

Villages & Vineyards of Alsace- Short Break

NZ$1760


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Andorra

Walking the Rugged Pyrenees of Andorra

NZ$1805


4.0 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 4
Challenging

Headwater
Navigation App

VIEW TRIP

Spain

Walking Mallorca's Mountains and Coast

NZ$1825


4.5 (4 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Andalucia

Walking the White Villages of the Alpujarras

NZ$1890


4.6 (7 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Headwater
Navigation App

VIEW TRIP

Portugal : Madeira

Walk the Garden Island of Madeira

NZ$1890


4.8 (4 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Greece

Walking on Kythnos Island

NZ$1915


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Italy : Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

NZ$1915

 
 

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Cyprus

Contrasts of Cyprus Walking

NZ$1960


4.6 (9 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+ to 2+

Headwater
Navigation App

VIEW TRIP

Italy

Undiscovered Puglia Walk - Discovering the South-East Coast

NZ$1980


4.8 (13 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Spain : Balearic Islands

Walking the Coastal Trails of Menorca

NZ$2000


4.6 (60 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Romania : Transylvania

Walking in Transylvania and the Carpathian Mountains

NZ$2000


4.9 (20 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

Switzerland : The Bernese Oberland

Walking in Kandersteg - Short Break

NZ$2090


4.9 (13 reviews)

VIEW TRIP

Self-guided walking

5 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : Mont Blanc

Mont Blanc Walks - Short Break

NZ$2110


4.5 (2 reviews)

VIEW TRIP

Self-guided walking

4 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Slovakia

Walking the Tatra Mountains in Slovakia

NZ$2110

NEW FOR 2026

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Catalonia

Contrasts of Catalunya Cycling - Short Break

NZ$2135


4.8 (8 reviews)

VIEW TRIP

Self-guided cycling

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

United Kingdom : Devon

Walking South Devon's Coastal Path

NZ$2200


5.0 (1 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

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Italy : Italian Lakes

Cycling Lake Garda by e-bike

NZ$2265


4.6 (5 reviews)

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Self-guided cycling

6 nights,
single centre

Level: 2+
Moderate plus

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United Kingdom : Wales

Highlights of the Gower Peninsula Walk

NZ$2310


5.0 (2 reviews)

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Self-guided walking

5 nights,
twin centre

Level: 1+
Leisurely plus

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Italy : Sardinia

Walking Sardinia's Green Coast

NZ$2310


5.0 (1 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

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Greece

Walking on Kythnos Island - Premium

NZ$2375


4.6 (7 reviews)

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Self-guided walking

6 nights,
twin centre

Level: 2+
Moderate plus

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France : Burgundy

Walking in Burgundy's Vineyards - Short Break

NZ$2400

 
 

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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France : The Pyrenees

Mediterranean Pyrenees Coastal Walk from Collioure to Cadaques

NZ$2400


5.0 (3 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

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Czechia

Walking through Bohemia

NZ$2420


4.9 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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France : Mont Blanc

Mont Blanc Walks - Short Break Premium

NZ$2440

 
 

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Self-guided walking

4 nights,
single centre

Level: 2+
Moderate plus

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United Kingdom : Wales

Walk the Welsh Highland Railway

NZ$2465


3.8 (4 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

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Andorra

Walk across Andorra

NZ$2485


4.7 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 4
Challenging

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Bosnia

Walking the Olympic Mountains of Bosnia

NZ$2510


5.0 (2 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

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Italy : Campania

Coastal Cilento Walk

NZ$2510


4.9 (9 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

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Austria : Salzburg

Walking the Tyrolean Mountains

NZ$2575


4.8 (4 reviews)

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Self-guided walking

6 nights,
single centre

Level: 2
Moderate

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Italy

Gems of the Amalfi Coast Walking

NZ$2575


4.8 (5 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

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Austria / Germany / Switzerland

Highlights of Lake Constance by bike

NZ$2595


4.9 (30 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

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Italy : Umbria

Walking on the Francigena Way

NZ$2620


4.6 (11 reviews)

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Self-guided pilgrimage

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

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United Kingdom

Walking in Jersey, Guernsey and Sark

NZ$2640


4.4 (16 reviews)

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Self-guided walking

6 nights,
twin centre

Level: 1+ & 2

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Spain : The Canary Islands

Walking in El Hierro

NZ$2660


4.5 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 2+

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Spain : Galicia

Highlights of the Camino de Santiago Walk

NZ$2705


4.8 (19 reviews)

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Self-guided pilgrimage

7 nights,
hotel-to-hotel

Headwater
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Switzerland

Walk the Crossroads of Five Passes

NZ$2795


4.9 (8 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 3

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Austria : The Tyrol

Alpine Walks in the Stubai Valley

NZ$2795


4.7 (12 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

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Italy : Tuscany

Wine & Walk in Chianti

NZ$2795


4.0 (2 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Greece : Crete

Cycling the Coast of Eastern Crete

NZ$2815


4.4 (5 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

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Spain : Valencia

Cycling Valencia and the Orange Blossom Coast

NZ$2860


4.6 (9 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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United Kingdom : Wales

Walking Offa's Dyke Path (South)

NZ$2860

 
 

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

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Spain : Galicia

Walking across the Pyrenees on the Camino Frances

NZ$2860


4.8 (5 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 : Catalonia

Classic Catalan Cycling

NZ$2880


4.8 (12 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Spain : The Canary Islands

Highlights of El Hierro Walk

NZ$2950


4.9 (11 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+ & 3

Headwater
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France : Burgundy

Walking in Burgundy's Vineyards

NZ$2970


4.8 (8 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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France : The French Riviera

The French Riviera Golden Islands

NZ$2970

NEW FOR 2026

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Self-guided walking

7 nights,
twin centre

Level: 1+
Leisurely plus

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France : Alsace

Villages & Vineyards of Alsace

NZ$3035


4.4 (7 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

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Germany : The Moselle

Meandering the Moselle Cycle Path

NZ$3080


4.0 (1 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

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Ireland

Unspoilt Ring of Kerry Cycling

NZ$3125


4.5 (6 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

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Spain : Rioja

Vineyards of La Rioja Cycling

NZ$3125


4.5 (8 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

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Portugal : The Algarve

Cycling the Algarve's Rota Vicentina

NZ$3125


4.9 (10 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

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France

Dordogne Activities

NZ$3125


4.8 (34 reviews)

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Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Switzerland : Valais

Walk in the Home of the Matterhorn

NZ$3145


5.0 (3 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 3

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Portugal : Mainland Portugal

Walk the Highlights of Northern Portugal

NZ$3145


4.5 (6 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

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Greece : Crete

Walking the Wonders of Crete

NZ$3170


3.7 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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Italy : Sicily

Sicily: Vino & Volcanoes

NZ$3190


5.0 (2 reviews)

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Cultural tour

7 nights,
hotel-to-hotel

Headwater
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Montenegro

Highlights of Southern Montenegro Walk

NZ$3190


5.0 (1 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

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Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

NZ$3255


4.0 (1 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
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Sweden : sweden

Cycling Stockholm's Archipelago

NZ$3280


4.3 (3 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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Spain : Extremadura

Cycling Central Spain in Style

NZ$3345


4.5 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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France : Mont Blanc

Walking Tour du Mont Blanc

NZ$3345

 
 

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Self-guided walking

7 nights,
twin centre

Level: 3
Stretching

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Croatia

Hike, Bike & Paddle Croatia

NZ$3365


4.0 (1 reviews)

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Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Portugal / Spain

Portugal Coastal Way to Santiago

NZ$3390


5.0 (11 reviews)

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Self-guided pilgrimage

14 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Portugal : Mainland Portugal

Cycling in Portugal: From the Mountains to the Sea

NZ$3500


4.5 (17 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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United Kingdom : Wales

Walking Offa's Dyke Path (North)

NZ$3585

 
 

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Self-guided walking

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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Norway

Walking in Balestrand

NZ$3610


4.3 (6 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
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United Kingdom : The Channel Islands

Walking in Jersey, Guernsey and Sark Premium

NZ$3650


5.0 (2 reviews)

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Self-guided walking

6 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
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Portugal : The Algarve

Walking the Algarve's South West

NZ$3785


4.9 (34 reviews)

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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Italy : Italian Lakes

Cycling the Italian Lakes

NZ$4090


4.9 (9 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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France : Mont Blanc

Walking Tour du Mont Blanc - Premium

NZ$4115


4.8 (6 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 3
Stretching

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Portugal : Mainland Portugal

Porto to Coimbra Cycling

NZ$4160


4.8 (56 reviews)

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Self-guided cycling

9 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Sweden / Denmark

Stockholm to Copenhagen Cycling

NZ$4225


4.2 (5 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Slovenia

Secrets of Slovenia Cycling

NZ$4335


4.9 (14 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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Italy : Puglia

Highlights of Puglia Cycling

NZ$4575


4.8 (13 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Portugal

Island Hopping in the Azores

NZ$4575


4.6 (5 reviews)

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Self-guided walking

14 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Iceland

Walking Iceland's Diamond Circle

NZ$5105


4.0 (1 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
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Canada : Sunshine Coast

Walking Canada's Sunshine Coast

NZ$5740


4.7 (3 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
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United Kingdom : Wales

Walking Offa's Dyke Path (North to South)

NZ$5810

 
 

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Self-guided walking

17 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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USA : Maine

Cycling Maine's Coast & National Park

NZ$7040

 
 

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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Japan

Japan: Hiroshima & Island Hopping

NZ$8205


5.0 (1 reviews)

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Multi-activity holiday

10 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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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.