AUTUMN ADVENTURES

As the summer crowds fade and landscapes turn golden, autumn is the perfect time to explore. Whether you're chasing autumnal colours, cosy escapes, or late-season sun, we've handpicked the best destinations to visit in September and October.

Below, we've put together a helpful list of our top picks for Autumn.

 

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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Slovenia

Lake Bled and Lake Bohinj Walk

NZ$1715


4.6 (31 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1+
Leisurely plus

Printed route
directions

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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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United Kingdom : Scotland

Walking the Rob Roy Way

NZ$2595

 
 

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

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United Kingdom : Scotland

Walking the West Highland Way

NZ$2640


4.3 (4 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

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France : Brittany

St. Malo to Mont-Saint-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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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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Italy : Italian Lakes

Walking at Lakes Orta and Maggiore

NZ$3300

NEW FOR 2025

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+ & 2

Headwater
Navigation App

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Portugal : Mainland Portugal

Cycling in the Douro Valley

NZ$3345

 
 

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

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Switzerland : The Bernese Oberland

Cycling the Swiss Lakes - Vevey to Lucerne

NZ$3805

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

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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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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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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France : The Loire

Chateaux Of The Loire Walk

NZ$2990


4.4 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

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Italy : Veneto

Walking in the Venetian Hills

NZ$2400


4.7 (90 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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

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Italy : Veneto

Venetian Villas and Vineyards Cycling

NZ$2905


4.7 (57 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

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Switzerland : The Bernese Oberland

Walking the Bernese Highlights West

NZ$3125


4.5 (2 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 4
Challenging

Navigation App

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Switzerland : The Bernese Oberland

Walking the Bernese Highlights East

NZ$3410


5.0 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

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Switzerland : Valais

Walking in Val D'Anniviers

NZ$3630


4.5 (2 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 3

Headwater
Navigation App

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Slovenia

Julian Alps to the Adriatic Cycling

NZ$4905


4.8 (126 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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United Kingdom : Northumberland

Walking the Best of Hadrian's Wall

NZ$1540


4.8 (29 reviews)

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Self-guided walking

5 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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United Kingdom : Cornwall

Walking the Lizard Peninsula

NZ$1915


4.3 (3 reviews)

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Self-guided walking

5 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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United Kingdom : Lake District

Literary Walking in the Lake District

NZ$2180


4.8 (36 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


4.9 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Switzerland : The Bernese Oberland

Classic Swiss Alps Walk

NZ$2485


4.8 (151 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

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

Spain : Galicia

Walking the Camino de Santiago

NZ$4070


4.6 (43 reviews)

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Self-guided pilgrimage

10 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Piedmont

Gastronomic Barolo Cycling by e-bike

NZ$4490


4.8 (89 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Walking the Green Coast of Minho

NZ$1300


4.0 (1 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

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Spain : Catalonia

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

Portugal : Mainland Portugal

Walking the Mountains, Valleys & Coast of Minho

NZ$1670


5.0 (3 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

Italy : Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

NZ$1805

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Northern Ireland

Walking the Antrim Way

NZ$1825

 
 

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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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

Portugal : Madeira

Walk the Garden Island of Madeira

NZ$1870


4.8 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Ireland

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

NZ$1935


4.0 (2 reviews)

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

Romania : Transylvania

Transylvanian Castles Walk

NZ$1935


4.9 (19 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Spain : Catalonia

Contrasts of Catalunya Cycling - Short Break

NZ$1980


4.8 (8 reviews)

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Self-guided cycling

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

VIEW TRIP

United Kingdom : Devon

Contrasts of Devon Walking

NZ$2025


4.5 (4 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

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

Slovakia

Walking the Tatra Mountains in Slovakia

NZ$2110

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Italy : Italian Lakes

Cycling Lake Garda with e-bike

NZ$2265


4.6 (5 reviews)

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Self-guided cycling

6 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Czechia

Walking through Bohemia

NZ$2310


4.9 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Devon

Walking South Devon's Coastal Path

NZ$2310


5.0 (1 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

France : The Loire

Multi Activity in the Loire

NZ$2330


5.0 (2 reviews)

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Multi-activity holiday

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

France : The Loire

Cycling The UNESCO Loire Valley

NZ$2355


5.0 (4 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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

Switzerland : The Bernese Oberland

Walking in Kandersteg - Short Break

NZ$2025


4.9 (12 reviews)

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Self-guided walking

5 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Andorra

Walk across Andorra

NZ$2400


4.7 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 4
Challenging

Headwater
Navigation App

VIEW TRIP

United Kingdom : Wales

Highlights of the Gower Peninsula Walk

NZ$2440


5.0 (2 reviews)

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Self-guided walking

5 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Cornwall

Walking the Western Tip of Cornwall

NZ$2530


4.9 (18 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

VIEW TRIP

United Kingdom : Wales

Walk the Welsh Highland Railway

NZ$2530


3.7 (3 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Switzerland : Davos

Walk the Crossroads of Five Passes

NZ$2530


4.9 (8 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 3

Headwater
Navigation App

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France : Normandy

D-Day Beaches Of Normandy Cycling

NZ$2640


4.6 (7 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

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Portugal : Mainland Portugal

Tour the Treasures of Portugal

NZ$2640


4.8 (5 reviews)

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Self-guided cultural tour

7 nights,
twin centre



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France : Normandy

Normandy Walk from Deauville to Bayeux

NZ$2685


4.8 (5 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

France : Mont Blanc

Mont Blanc Walks - Short Break Premium

NZ$2795

 
 

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Self-guided walking

4 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

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Ireland

Walking and Cycling the Wild Atlantic Way

NZ$2815

 
 

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Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

VIEW TRIP

France : Burgundy

Walking in Burgundy's Vineyards

NZ$2815


4.8 (8 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

United Kingdom : Norfolk

Highlights of Norfolk Cycling

NZ$2840


4.4 (11 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

VIEW TRIP

France : The Dordogne

Canoeing on the Dordogne

NZ$2860


4.9 (56 reviews)

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8 nights,
hotel-to-hotel

Printed route
directions



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France : Canal du Midi

Canal du midi Cycling : from Toulouse to Sete

NZ$2905


4.8 (5 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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France : The Loire

Canoeing on the Loire

NZ$2925


4.0 (1 reviews)

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5 nights,
hotel-to-hotel

Navigation App



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France : Burgundy

Cycling the Vineyards From Beaune to Macon

NZ$2925


4.8 (6 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

VIEW TRIP

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

VIEW TRIP

France : The Loire

Cycling The Chateaux Of The Loire - Upgraded Short

NZ$2950


4.8 (4 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

VIEW TRIP

United Kingdom : Wales

Walking Offa's Dyke Path (South)

NZ$2970

 
 

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Walk the Highlights of Northern Portugal

NZ$3015


4.5 (6 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

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
Navigation App

VIEW TRIP

Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

NZ$3210

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Portugal Coastal Way to Santiago

NZ$3235


5.0 (11 reviews)

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Self-guided pilgrimage

14 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

VIEW TRIP

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
Navigation App

VIEW TRIP

Portugal : Mainland Portugal

Cycling in Portugal: From the Mountains to the Sea

NZ$3365


4.5 (17 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

Norway

Walking in Balestrand

NZ$3610


4.6 (5 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

VIEW TRIP

United Kingdom : Wales

Walking Offa's Dyke Path (North)

NZ$3650

 
 

VIEW TRIP

Self-guided walking

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

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

VIEW TRIP

United Kingdom : The Cotswolds

Best of the Cotswolds Cycling

NZ$3785


4.0 (1 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

VIEW TRIP

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

VIEW TRIP

Denmark

Nordic Cities by Rail

NZ$4025

NEW FOR 2025

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Self-guided cultural tour

9 nights,
hotel-to-hotel



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Slovenia

Secrets of Slovenia Cycling

NZ$4070


4.9 (14 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

France : Mont Blanc

Walking Tour du Mont Blanc - Premium

NZ$4115


4.8 (5 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 3
Stretching

Headwater
Navigation App

VIEW TRIP

Iceland

Walking Iceland's Diamond Circle

NZ$5060

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

VIEW TRIP

Canada : Sunshine Coast

Walking Canada's Sunshine Coast

NZ$5740


4.7 (3 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

VIEW TRIP

USA : Maine

Cycling Maine's Coast & National Park

NZ$7040

 
 

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

VIEW TRIP

Japan

Walk the Nakasendo Trail

NZ$7480

 
 

VIEW TRIP

Self-guided walking

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

VIEW TRIP

Faroe Islands

Walking the Faroe Islands - With Private Guide

NZ$8120

NEW FOR 2025

VIEW TRIP

Private guided walking

7 nights,
single centre

Level: 2+
Moderate plus

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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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