NEW Holidays for 2025

Showing 50 out of 329 trips

Look ahead to a host of spectacular new holidays in 2025, as our teams have been working behind the scenes to introduce new handcrafted itineraries.

Our brand-new walking holiday on the Italian Lakes is already proving popular with the Headwater community as you stay on the stunning Lakes Maggiore & Orta, exploring medieval villages, vineyards, and of course sampling the unbeatable local cuisine!

If you're more comfortable on two wheels, our new E-Bike Across Southern Albania trip journeys from mountains to coast across this lesser-discovered country, described by National Geographic as 'Europe's Rising Star'.

Our new holidays continue to offer you a fresh perspective on some of our most-loved Headwater destinations, allowing you time to focus on uncovering hidden gems, sampling the delicious local cuisine and creating those magical moments while we take care of the rest.

Walk the glorious island of Gozo, explore the mighty Triglav National Park in Slovenia's Julian Alps, or meander the idyllic coastline of Fuerteventura.

Hop on your bike and cycle from Coimbra to Lisbon, traverse the Adriatic Coast from Venice to Porec, or meander along the designated Moselle Cycle Path.

If you fancy taking to the water, we have exceptional multi-activity holidays which feature a mix of walking, cycling and kayaking or canoeing; a unique way to discover a new destination.

Canoe the peaceful French waters of the Loire River, hike, bike & paddle Croatia's National Parks, or venture further afield to discover the Sunshine Coast of Canada where lush rainforest, protected inlets, and waterfront retreats await.

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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

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
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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

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

Austria : The Tyrol

Walking the Kitzbühel Alps Trail

NZ$2220

NEW FOR 2025

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

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

Albania

E-bike Across Southern Albania

NZ$2620

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

Germany : Saxon Switzerland

Walking in the Elbe Sandstone Mountains

NZ$2660

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

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
Moderate

Headwater
Navigation App

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

Switzerland : The Bernese Oberland

Cycling the Swiss Lakes - Vevey to Lucerne

NZ$3785

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

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

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

Norway

Cycling Norway's Fjords: Hardangerfjord from Bergen

NZ$5455

NEW FOR 2025

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

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

Norway

Cycling the Norwegian Archipelago South of Bergen

NZ$6180

NEW FOR 2025

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

Norway

Walking Norway's Fjords: Hardangerfjord from Bergen

NZ$6865

NEW FOR 2025

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

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

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

Holland

Cycling from Amsterdam

NZ$1850

NEW FOR 2025

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Self-guided cycling

3 nights,
single centre

Level: 1+
Leisurely plus

Navigation App

France : Burgundy

Tour de France - Burgundy

NZ$2045

NEW FOR 2025

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Self-guided cycling

3 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

France : Provence

Tour de France - Provence

NZ$2090

NEW FOR 2025

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Self-guided cycling

3 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

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

Italy : Istria

Walking the Highlights of Istria: Italy, Slovenia & Croatia

NZ$2200

NEW FOR 2025

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Italy : Sardinia

Walking Sardinia's Green Coast

NZ$2265

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Germany : Bavaria

Walking the Black Forest to Lake Constance

NZ$2310

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Italy : The Dolomites

Cross country skiing in the Dolomites

NZ$2400

NEW FOR 2025

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Winter snow holiday

7 nights,
single centre



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

Bosnia

Walking the Olympic Mountains of Bosnia

NZ$2620

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Greece : Peloponnese

Peloponnese Coast and Mountain Walking

NZ$2660

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

France : The Loire

Tour de France - Loire

NZ$2815

NEW FOR 2025

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

Germany : The Moselle

Meandering the Moselle Cycle Path

NZ$2970

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

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

France : Canal du Midi

Tour de France - Canal du Midi

NZ$3060

NEW FOR 2025

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Self-guided cycling

4 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

Norway : Gudbrandsdalen

Cross Country Skiing at Rondane National Park

NZ$3080

NEW FOR 2025

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Winter snow holiday

5 nights,
single centre



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

France : Alsace

Cycling the Scenic Rhine: Strasbourg to Mainz

NZ$3125

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

NZ$3210

NEW FOR 2025

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Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

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

Spain : Extremadura

Cycling Central Spain in Style

NZ$3280

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

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

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

Denmark

Nordic Cities by Rail

NZ$4025

NEW FOR 2025

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Self-guided cultural tour

9 nights,
hotel-to-hotel



Morocco

Morocco: Mountains, Desert & Coast

NZ$4795

NEW FOR 2025

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Self-guided cultural tour

7 nights,
hotel-to-hotel



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

Iceland

An Icelandic Adventure

NZ$5455

NEW FOR 2025

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Self-guided cultural tour

7 nights,
hotel-to-hotel



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

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

Peru

Walking Machu Picchu - With Private Guide

NZ$9350

NEW FOR 2025

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Private guided walking

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

France

Tour de France

NZ$11570

NEW FOR 2025

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Self-guided cycling

20 nights,
hotel-to-hotel

Level: 2 & 3

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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.