Coastal Gems

Showing 144 out of 333 trips

From the sun-kissed beaches of the Algarve to the vertical landscape of dramatic pastel villages clinging to hillsides on the Sorrentine peninsula, discover the wonders of the coast on one of our coastal escapes. You'll experience hidden coves, turquoise seas and colourful fishing harbours, with excellent seafood specialities. Spend your evenings in hand-picked hotels right by the sea.

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Malta + Gozo : Malta

Walking on Glorious Gozo - Short Break

NZ$1275

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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Malta + Gozo

Highlights of Secrets of Malta Walking

NZ$1340


4.5 (2 reviews)

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Self-guided walking

4 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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United Kingdom : Devon

The English Riviera & Dart Valley Walk

NZ$1450


5.0 (1 reviews)

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Self-guided walking

4 nights,
twin centre

Level: 2
Moderate

Printed route
directions

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United Kingdom : The Channel Islands

Walking in Guernsey and Sark

NZ$1475

NEW FOR 2025

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Self-guided walking

3 nights,
single centre

Level: 1+ & 2

Headwater
Navigation App

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United Kingdom : The Channel Islands

Walking in Jersey Premium

NZ$1605

NEW FOR 2025

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Self-guided walking

3 nights,
single centre

Level: 1+ & 2

Headwater
Navigation App

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Malta + Gozo : Malta

Walking on Glorious Gozo

NZ$1670

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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Malta + Gozo

Discovering the Maltese Islands

NZ$1850


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

Walking the trails of Tenerife

NZ$1935


4.5 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2 & 3

Headwater
Navigation App

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Spain : The Canary Islands

Walk the Bonita Island of La Palma

NZ$0

NEW FOR 2025

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Self-guided walking

7 nights,
single centre

Level: 2 & 2+

Headwater
Navigation App

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Denmark

Cycling from Copenhagen

NZ$2245


5.0 (1 reviews)

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Self-guided cycling

4 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

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Spain : The Canary Islands

Contrasts of Lanzarote

NZ$2290


5.0 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : Puglia

Cycling the Heel of Italy - Alberobello to Lecce

NZ$2310


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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Spain : The Canary Islands

Contrasts of La Gomera

NZ$2310


4.2 (5 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Portugal : Madeira

Walking the Waterways and villages of Madeira

NZ$2330


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

Walking on Gran Canaria

NZ$2400


5.0 (7 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : The Bay of Naples

The Islands of Amalfi Walk

NZ$2440


4.6 (14 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 in Fuerteventura along the GR 131

NZ$2510

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Headwater
Navigation App

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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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Italy : Puglia

Journey through Puglia to Matera

NZ$2530


4.8 (13 reviews)

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Self-guided cultural tour

7 nights,
hotel-to-hotel

Headwater
Navigation App

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Croatia

Dalmatian Coast Island Hopping

NZ$2705


4.8 (20 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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France : Brittany

St Malo to Mont St Michel Cycling

NZ$2860

 
 

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Croatia

Dalmatian Islands Walk

NZ$2950


4.9 (9 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+ & 2

Printed route
directions

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Spain : The Canary Islands

Walking across La Gomera

NZ$2950

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 3

Headwater
Navigation App

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France : Normandy

Normandy Walk from Deauville to Bayeux - Deluxe

NZ$3015


5.0 (2 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

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Portugal : The Algarve

Walking Rota Vicentina North Fishermen's Trail

NZ$3060


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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Greece : Crete

Cycling in the Peloponnese

NZ$3100


4.8 (12 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Trentino

Brenner Pass to Venice Cycling

NZ$3235


5.0 (2 reviews)

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Self-guided cycling

9 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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United Kingdom : The Channel Islands

Cycling in Jersey, Guernsey and Sark

NZ$3390


4.0 (1 reviews)

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Self-guided cycling

6 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy : Puglia

Cycling the Heel of Italy - Matera to Lecce

NZ$3585


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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France : Atlantic Coast

Cycling along the Atlantic Coast

NZ$4050

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Spain : The Canary Islands

Contrasts of Tenerife Walk (with transfers)

NZ$4290

 
 

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Self-guided walking

7 nights,
twin centre

Level: 1+ to 2+

Headwater
Navigation App

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Portugal : Mainland Portugal

Coimbra to Lisbon Cycling

NZ$4380

NEW FOR 2025

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Norway

Cycling Norway's Fjords: Hardangerfjord from Bergen

NZ$5765

NEW FOR 2025

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

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Canada : Sunshine Coast

Walk & Paddle Canada's Sunshine Coast

NZ$5960

NEW FOR 2025

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Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 1+ to 3

Headwater
Navigation App

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Norway

Cycling the Norwegian Archipelago South of Bergen

NZ$6510

NEW FOR 2025

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

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Norway

Walking Norway's Fjords: Hardangerfjord from Bergen

NZ$7170

NEW FOR 2025

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

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Norway

Cycling in the Lofoten Islands

NZ$8450


5.0 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Sicily

Walking the Highlights of Western Sicily

NZ$2485

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : The Bay of Naples

The Amalfi Coast Walk

NZ$4885


4.8 (90 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Sicily

Volcanoes of Sicily Walk

NZ$3365


4.4 (12 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : Corsica

North Corsican Wonders Between Coast and Mountains

NZ$2840


4.0 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Printed route
directions

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Malta + Gozo

Walking on Gozo - Calypso's Isle

NZ$1915


4.6 (143 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

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Spain : The Canary Islands

Contrasts of Tenerife Walk (with car hire)

NZ$2795


4.7 (11 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 1+ to 2+

Headwater
Navigation App

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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 : The Bay of Naples

Walking Amalfi's Path of the Gods

NZ$1980


5.0 (2 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Italy : Veneto

Bolzano, Verona & Venice Ride

NZ$2465


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 (64 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Italy : Sicily

Secrets of Sicily Cycling

NZ$2770


4.6 (24 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

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 : The Algarve

Cycling in The Real Algarve

NZ$3125


4.7 (66 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Sicily

Cycling through Baroque Sicily

NZ$3500


4.5 (22 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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United Kingdom : Cornwall

Walking the Lizard Peninsula

NZ$1915


4.0 (2 reviews)

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Self-guided walking

5 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Spain : Catalonia

Catalan Classic Walk

NZ$2180


4.7 (79 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Cornwall

Walking Cornwall's North coast Padstow to Perranporth

NZ$2245

 
 

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Self-guided walking

5 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Ireland

Walking the Kerry Way and Killarney N.P.

NZ$2510


4.8 (6 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Portugal : The Algarve

Walk the Algarve's Wild West

NZ$2595


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

Spain : Catalonia

Contrasts of Catalunya Cycling

NZ$2795


4.7 (56 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

United Kingdom : Wales

Highlights of the Pembrokeshire Coast

NZ$2840


3.9 (8 reviews)

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Self-guided walking

6 nights,
twin centre

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Spain : Balearic Islands

Cycling in Mallorca: Coast to Coast

NZ$2950


4.7 (34 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

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$3235


4.6 (125 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Norfolk

Contrasts of Norfolk Cycling

NZ$3410


5.0 (1 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Porto Coastal Cycling

NZ$3410


4.4 (59 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Croatia

Coastal Croatia - Porec to Pula Cycling

NZ$3475


4.7 (86 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Walking the Green Coast of Minho

NZ$1300


4.0 (1 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

VIEW TRIP

Malta + Gozo : Malta

Walking on Gozo - Calypso's Isle - Short Break

NZ$1320


4.7 (10 reviews)

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Self-guided walking

4 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Spain

Catalan Classic Walk - Short Break

NZ$1670


4.7 (7 reviews)

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Cyprus

Walking the Akamas Peninsula

NZ$1670


4.5 (11 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 1 & 2

Headwater
Navigation App

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United Kingdom : Devon

Walking Devon's Coastal Highlights

NZ$1695


4.0 (1 reviews)

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Malta + Gozo : Malta

Secrets of Malta Walking

NZ$1740


5.0 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Liguria

Walking in the Cinque Terre and Portofino

NZ$1850


4.3 (7 reviews)

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Self-guided walking

6 nights,
single centre

Level: 2
Moderate

Navigation App

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United Kingdom : Dorset

Jewels of the Jurassic Coast Walk

NZ$1870


4.3 (3 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Greece

Walking on Kythnos Island

NZ$1890


5.0 (2 reviews)

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Self-guided walking

6 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

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

VIEW TRIP

Ireland

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

NZ$1935


4.0 (2 reviews)

VIEW TRIP

Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

Portugal : Madeira

Walk the Garden Island of Madeira

NZ$1935


4.8 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Catalonia

Contrasts of Catalunya Cycling - Short Break

NZ$1980


4.7 (6 reviews)

VIEW TRIP

Self-guided cycling

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

Spain : Balearic Islands

Walking the Coastal Trails of Menorca

NZ$2000


4.6 (60 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

United Kingdom : Devon

Contrasts of Devon Walking

NZ$2025


4.7 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Spain : Balearic Islands

Walking Mallorca's Mountains and Coast

NZ$2025


3.3 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Puglia

Undiscovered Puglia Walk - Discovering the South-East Coast

NZ$2070


4.8 (13 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

France : Normandy

Normandy Walk from Deauville to Bayeux

NZ$2245


4.8 (5 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

United Kingdom : Wales

North Pembrokeshire Coast Walk

NZ$2310

 
 

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 2+ & 3

Printed route
directions

VIEW TRIP

United Kingdom : Devon

Walking South Devon's Coastal Path

NZ$2310


5.0 (1 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Sweden : sweden

Cycling from Stockholm

NZ$2355

 
 

VIEW TRIP

Self-guided cycling

5 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Greece

Walking on Kythnos Island - Premium

NZ$2355


4.6 (7 reviews)

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

France : The Pyrenees

Mediterranean Pyrenees Coastal Walk from Collioure to Cadaques

NZ$2375


5.0 (3 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Sardinia

Walking Sardinia's Green Coast

NZ$2375

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Veneto

Adriatic Coast - Venice to Porec Ride

NZ$2420

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

United Kingdom : Wales

Highlights of the Gower Peninsula Walk

NZ$2440


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

5 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Italy : Campania

Coastal Cilento Walk

NZ$2485


4.9 (8 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Cornwall

Walking the Western Tip of Cornwall

NZ$2530


4.9 (18 reviews)

VIEW TRIP

Self-guided walking

6 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

VIEW TRIP

Italy : The Bay of Naples

Gems of the Amalfi Coast Walking

NZ$2620


4.8 (4 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : Normandy

D-Day Beaches Of Normandy Cycling

NZ$2640


4.6 (7 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

VIEW TRIP

Greece : Peloponnese

Peloponnese Coast and Mountain Walking

NZ$2660

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Greece : Crete

Cycling the Coast of Eastern Crete

NZ$2685


4.4 (5 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

United Kingdom : The Channel Islands

Walking in Jersey, Guernsey and Sark

NZ$2685


4.4 (15 reviews)

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 1+ & 2

Headwater
Navigation App

VIEW TRIP

Spain : The Canary Islands

Highlights of El Hierro Walk

NZ$2705


4.9 (11 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+ & 3

Headwater
Navigation App

VIEW TRIP

Spain : Catalonia

Classic Catalan Cycling

NZ$2750


4.8 (12 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Ireland

Walking and Cycling the Wild Atlantic Way

NZ$2815

 
 

VIEW TRIP

Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

United Kingdom : Norfolk

Highlights of Norfolk Cycling

NZ$2840


4.3 (10 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Spain : Valencia

Cycling Valencia and the Orange Blossom Coast

NZ$2880


4.6 (9 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Ireland : County Wicklow

Unspoilt Ring of Kerry Cycling

NZ$2925


4.4 (5 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Montenegro

Highlights of Southern Montenegro Walk

NZ$2925


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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Spain

Walking in El Hierro

NZ$2860


4.5 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 2+

Headwater
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Portugal : Mainland Portugal

Walk the Highlights of Northern Portugal

NZ$3015


4.5 (6 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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France : The French Riviera

The French Riviera Golden Islands

NZ$3035

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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Sweden : sweden

Cycling Stockholm's Archipelago

NZ$3080


5.0 (1 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Spain : Balearic Islands

Walking Mallorca trails and traditional Fincas

NZ$3100

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Portugal : The Algarve

Cycling the Algarve's Rota Vicentina

NZ$3210


4.9 (9 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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Portugal : Mainland Portugal

Portugal Coastal Way to Santiago

NZ$3235


5.0 (9 reviews)

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Self-guided pilgrimage

14 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Croatia

Hike, Bike & Paddle Croatia

NZ$3255

NEW FOR 2025

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Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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France : Atlantic Coast

Tour de France - Atlantic Coast

NZ$3300

NEW FOR 2025

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2 & 2+

Navigation App

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Portugal : Mainland Portugal

Cycling in Portugal: From the Mountains to the Sea

NZ$3365


4.5 (16 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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Italy : Sardinia

Undiscovered Sardinia Cycling

NZ$3410


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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United Kingdom : The Channel Islands

Walking in Jersey, Guernsey and Sark Premium

NZ$3455


5.0 (2 reviews)

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Self-guided walking

6 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
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Greece : Crete

Walking the Wonders of Crete

NZ$3540

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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France : Normandy

Paris to the Sea Along the Seine River

NZ$3740

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

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Portugal : The Algarve

Walking the Algarve's South West

NZ$3940


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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Sweden : sweden

Stockholm to Copenhagen Cycling

NZ$3980


4.3 (4 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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France : Corsica

Corsica with Ebike

NZ$4005


4.7 (3 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2 & 2+

Printed route
directions

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Portugal : Mainland Portugal

Porto to Coimbra Cycling

NZ$4025


4.8 (56 reviews)

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Self-guided cycling

9 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Italy

Highlights of Puglia Cycling

NZ$4530


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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Portugal : The Azores

Island Hopping in the Azores

NZ$4575


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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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
Navigation App

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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
Navigation App

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Japan

Japan: Hiroshima & Island Hopping

NZ$7700

NEW FOR 2025

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Multi-activity holiday

10 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Faroe Islands

Walking the Faroe Islands - With Private Guide

NZ$8120

NEW FOR 2025

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Private guided walking

7 nights,
single centre

Level: 2+
Moderate plus

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Cyprus

Walking in North Cyprus

NZ$2090


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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Greece

Mountains & Villages of Evia

NZ$2420


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

NZ$3190


4.7 (11 reviews)

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Guided group walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

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Greece

Walking on the Greek Islands

NZ$3190

 
 

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Guided group walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

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Italy : Puglia

Walking in Puglia & Matera

NZ$3300


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

NZ$3520


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

NZ$3740

 
 

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Guided group walking

11 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

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Portugal : Mainland Portugal

Porto to Lisbon Atlantic Ride

NZ$3840

 
 

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Guided group cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Croatia

Cycling Croatia's Dalmatian Coast

NZ$3950

 
 

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Guided group cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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France : The French Riviera

Walks & Gardens of the French Riviera

NZ$4290


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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Portugal : The Azores

Walking in the Azores

NZ$4840

 
 

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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

NZ$5060

 
 

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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

NZ$5280


4.5 (2 reviews)

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Guided group walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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South Africa

Cycling the Cape & Winelands

NZ$5940

 
 

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Guided group cycling

11 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

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Iceland

Iceland Explorer

NZ$7260

 
 

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Guided group walking

9 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Peru

Peru Explorer

NZ$10340

 
 

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Guided group walking

19 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.