The Winter Sun Collection

As the winter weather rolls in, there’s no need to get summer blues when you can get winter sun instead. Our holidays to hot destinations will keep you in shorts and flip-flops instead of hats and scarves. From the pink sand beaches of Bermuda to the colourful towns of the Amalfi Coast , our selection of active cycling and walking holidays below are all guaranteed to keep you in the heat.

 

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

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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

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Malta + Gozo

Discovering the Maltese Islands

NZ$1780


4.3 (10 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

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

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Spain : Andalucia

Walking in Sierra de Aracena

NZ$2090


4.8 (15 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

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Spain : The Canary Islands

Walking the trails of Tenerife

NZ$2110


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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Spain : The Canary Islands

Walking in Fuerteventura along the GR 131

NZ$2265


5.0 (2 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Headwater
Navigation App

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Italy : Puglia

Cycling the Heel of Italy - Alberobello to Lecce

NZ$2290


4.7 (44 reviews)

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Self-guided cycling

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$2375


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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Spain : The Canary Islands

Contrasts of La Gomera

NZ$2400


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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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

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Spain : The Canary Islands

Volcanoes and Vineyards of Lanzarote

NZ$2510


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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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

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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 & 3

Headwater
Navigation App

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Italy : Puglia

Cycling the Heel of Italy - Matera to Lecce

NZ$3610


4.7 (14 reviews)

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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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

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Portugal : Mainland Portugal

Coimbra to Lisbon Cycling

NZ$4380

 
 

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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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

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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 : Veneto

Bolzano, Verona & Venice Ride

NZ$2485


4.7 (20 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Puglia

Self Guided Walking in Puglia: From Lecce to Matera

NZ$2575


4.7 (65 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

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Italy : Tuscany

A Taste of Tuscany Walking

NZ$2795


4.9 (31 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : Tuscany

A Taste of Tuscany Cycling

NZ$2905


4.9 (28 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Portugal : The Algarve

Cycling in The Real Algarve

NZ$3080


4.7 (66 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Bermuda

Islands of Bermuda Walk

NZ$3100


4.6 (38 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

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Portugal : Madeira

Marvels of Madeira Walk

NZ$3280


4.7 (126 reviews)

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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

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

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Austria : The Danube

Cycling from Vienna to Budapest

NZ$2620


4.6 (66 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Spain : Balearic Islands

Cycling in Mallorca: Coast to Coast

NZ$2860


4.7 (35 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Spain : Andalucia

Cycling in Andalucia: Seville to Cadiz

NZ$3190


4.4 (17 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

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Italy : Puglia

Contrasts of Puglia Cycling

NZ$3190


4.6 (126 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Spain : Andalucia

Hidden Valleys of Cordoba Walk

NZ$1275


4.8 (55 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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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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Malta + Gozo : Malta

Secrets of Malta Walking

NZ$1670


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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Italy : Veneto

Walking in the Prosecco Hills

NZ$1715

NEW FOR 2026

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Self-guided walking

5 nights,
hotel-to-hotel

Level: 1+ & 2

Navigation App

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Italy : Liguria

Walking in the Cinque Terre and Portofino

NZ$1890


4.3 (7 reviews)

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Self-guided walking

6 nights,
single centre

Level: 2
Moderate

Navigation App

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Portugal : Madeira

Walk the Garden Island of Madeira

NZ$1890


4.8 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Cyprus

Contrasts of Cyprus Walking

NZ$1890


4.6 (8 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+ to 2+

Headwater
Navigation App

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Italy

Undiscovered Puglia Walk - Discovering the South-East Coast

NZ$1980


4.8 (13 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : Istria

Walking the Highlights of Istria: Italy, Slovenia & Croatia

NZ$2330


5.0 (2 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Tuscany

Cycling in Tuscany: Pisa to Florence

NZ$2440


4.7 (9 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Austria : The Danube

Cycling along the Danube from Passau to Vienna

NZ$2465


4.9 (28 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Spain : Balearic Islands

Walking Mallorca trails and traditional Fincas

NZ$2595

 
 

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Campania

Coastal Cilento Walk

NZ$2640


4.9 (9 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Italy : Italian Lakes

Cycling Lake Garda by e-bike

NZ$2660


4.6 (5 reviews)

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Self-guided cycling

6 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Spain

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+

Headwater
Navigation App

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Italy : The Bay of Naples

Gems of the Amalfi Coast Walking

NZ$2705


4.8 (5 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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France : The French Riviera

The French Riviera Golden Islands

NZ$2730

NEW FOR 2026

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Self-guided walking

7 nights,
twin centre

Level: 1+ & 2

Headwater
Navigation App

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Italy : Umbria

Walking on the Francigena Way

NZ$2750


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 : 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
Navigation App

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Italy : Sardinia

Undiscovered Sardinia Cycling

NZ$3060


4.7 (19 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Portugal : The Algarve

Cycling the Algarve's Rota Vicentina

NZ$3125


4.9 (9 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Spain : Extremadura

Cycling Central Spain in Style

NZ$3280


4.5 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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Austria : The Danube

Passau to Vienna Cycling

NZ$3300


4.8 (77 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

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Cape Verde

Cape Verde's Northern Islands - With Private Guide

NZ$3760


4.9 (7 reviews)

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Private guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

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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

Headwater
Navigation App

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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
Navigation App

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Morocco

Morocco: Mountains, Desert & Coast

NZ$4445

 
 

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Cultural tour

7 nights,
hotel-to-hotel



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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
Navigation App

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Japan

Shikoku Pilgrimage Trail

NZ$7325


5.0 (1 reviews)

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Self-guided pilgrimage

10 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

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Japan

Walk the Kumano Kodo

NZ$7390


5.0 (4 reviews)

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

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China

Walking the Charms of China - With Private Guide

NZ$7700

 
 

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Private guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

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Japan

Walk the Nakasendo Trail

NZ$7965

 
 

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

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Japan

Exploring the land of Shogun and Samurai

NZ$8535

NEW FOR 2026

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Cultural tour

10 nights,
hotel-to-hotel

8 meals
included

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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.

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