NEW Holidays for 2025

Showing 42 out of 337 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.

Gozo

Walking on Glorious Gozo - Short Break

AU$945

NEW FOR 2025

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Self-guided walking

4 nights,
single centre

Level: 1+
Leisurely plus

Headwater
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United Kingdom : The Channel Islands

Walking in Guernsey and Sark

AU$1170

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

AU$1290

NEW FOR 2025

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Self-guided walking

3 nights,
single centre

Level: 1+ & 2

Headwater
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Gozo

Walking on Glorious Gozo

AU$1290

NEW FOR 2025

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Self-guided walking

7 nights,
single centre

Level: 1+
Leisurely plus

Headwater
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Spain : The Canary Islands

Walking in Fuerteventura along the GR 131

AU$2130

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Headwater
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Albania

E-bike Across Southern Albania

AU$2235

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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Germany : Saxon Switzerland

Walking in the Elbe Sandstone Mountains

AU$2275

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

AU$2540

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

AU$2870

NEW FOR 2025

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+ & 2

Headwater
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France : Atlantic Coast

Cycling along the Atlantic Coast

AU$3565

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

Portugal : Mainland Portugal

Coimbra to Lisbon Cycling

AU$3875

NEW FOR 2025

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Canada : Sunshine Coast

Walk & Paddle Canada’s Sunshine Coast

AU$5350

NEW FOR 2025

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Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 1+ to 3

Headwater
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Italy : Sicily

Walking the Highlights of Western Sicily

AU$2050

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
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Italy : Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

AU$1475

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

Headwater
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Holland

Cycling from Amsterdam

AU$1560

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

AU$1700

NEW FOR 2025

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Self-guided cycling

3 nights,
hotel-to-hotel

Level: 2+
Moderate plus

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France : Provence

Tour de France - Provence

AU$1745

NEW FOR 2025

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Self-guided cycling

3 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

Italy : The Dolomites

Cross country skiing in the Dolomites

AU$1845

NEW FOR 2025

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Winter snow holiday

7 nights,
single centre

Italy : Sardinia

Walking Sardinia's Green Coast

AU$1905

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Italy : Veneto

Adriatic Coast - Venice to Poreč Ride

AU$1970

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Germany : Bavaria

Walking the Black Forest to Lake Constance

AU$2050

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Spain : Balearic Islands

Walking Mallorca trails and traditional Fincas

AU$2195

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Bosnia

Walking the Olympic Mountains of Bosnia

AU$2235

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

AU$2420

NEW FOR 2025

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 3
Stretching

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Spain : Andalucia

E-biking in Andalucia: Sierra de Aracena

AU$2420

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Norway : Gudbrandsdalen

Cross Country Skiing at Rondane National Park

AU$2420

NEW FOR 2025

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Winter snow holiday

5 nights,
single centre

Croatia

Hike, Bike & Paddle Croatia

AU$2480

NEW FOR 2025

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Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Germany : The Moselle

Meandering the Moselle Cycle Path

AU$2565

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

AU$2625

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

AU$2645

NEW FOR 2025

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Self-guided cycling

4 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

AU$2790

NEW FOR 2025

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Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

Spain : Extremadura

Cycling Central Spain in Style

AU$2850

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

AU$2870

NEW FOR 2025

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2 & 2+

Navigation App

Greece

Walking the Wonders of Crete

AU$2950

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

France : Normandy

Paris to the Sea Along the Seine River

AU$3280

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

AU$3485

NEW FOR 2025

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Self-guided cultural tour

9 nights,
hotel-to-hotel

Morocco

Morocco: Mountains, Desert & Coast

AU$4265

NEW FOR 2025

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Self-guided cultural tour

7 nights,
hotel-to-hotel

Iceland

Walking Iceland's Diamond Circle

AU$4510

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

AU$4880

NEW FOR 2025

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Self-guided cultural tour

7 nights,
hotel-to-hotel

Japan

Japan: Hiroshima & Island Hopping

AU$6970

NEW FOR 2025

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Multi-activity holiday

10 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Peru

Walking Machu Picchu - With Private Guide

AU$8510

NEW FOR 2025

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Private guided walking

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

AU$10580

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.