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NEW Holidays for 2025

Showing 52 out of 330 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.

New walking holidays for 2025

New cycling holidays for 2025

New Private Guided Walks

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Malta + Gozo : Malta

Walking on Glorious Gozo - Short Break

£579

NEW FOR 2025

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Self-guided walking

4 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

United Kingdom : The Channel Islands

Walking in Guernsey and Sark

£669

NEW FOR 2025

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Self-guided walking

3 nights,
single centre

Level: 1+ & 2

Headwater
Navigation App

£250 SAVING - T&CS APPLY

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United Kingdom : The Channel Islands

Walking in Jersey Premium

£729

NEW FOR 2025

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Self-guided walking

3 nights,
single centre

Level: 1+ & 2

Headwater
Navigation App

£250 SAVING - T&CS APPLY

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Malta + Gozo : Malta

Walking on Glorious Gozo

£759

NEW FOR 2025

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Self-guided walking

7 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

£250 SAVING - T&CS APPLY

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Austria : The Tyrol

Walking the Kitzbuhel Alps Trail

£1009

NEW FOR 2025

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

£250 SAVING - T&CS APPLY

VIEW TRIP

Spain : The Canary Islands

Walking in Fuerteventura along the GR 131

£1139

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Headwater
Navigation App

#250 SAVING - T&CS APPLY

VIEW TRIP

Albania

E-bike Across Southern Albania

£1189

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

Germany : Bavaria

Walking in the Elbe Sandstone Mountains

£1209

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

£250 SAVING - T&CS APPLY

VIEW TRIP

Spain : The Canary Islands

Walking across La Gomera

£1339

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

#250 SAVING - T&CS APPLY

VIEW TRIP

Italy : Italian Lakes

Walking at Lakes Orta and Maggiore

£1499

NEW FOR 2025

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+ & 2

Headwater
Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

Switzerland : The Bernese Oberland

Cycling the Swiss Lakes - Vevey to Lucerne

£1729

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

France : Atlantic Coast

Cycling along the Atlantic Coast

£1839

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

Portugal : Mainland Portugal

Coimbra to Lisbon Cycling

£1989

NEW FOR 2025

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

Norway

Cycling Norway's Fjords: Hardangerfjord from Bergen

£2599

NEW FOR 2025

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

£250 SAVING - T&CS APPLY

VIEW TRIP

Canada : Sunshine Coast

Walk & Paddle Canada's Sunshine Coast

£2709

NEW FOR 2025

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Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 1+ to 3

Headwater
Navigation App

#250 SAVING - T&CS APPLY

VIEW TRIP

Norway

Cycling the Norwegian Archipelago South of Bergen

£2869

NEW FOR 2025

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

£250 SAVING - T&CS APPLY

VIEW TRIP

Norway

Walking Norway's Fjords: Hardangerfjord from Bergen

£3119

NEW FOR 2025

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2 & 3

Printed route
directions

#250 SAVING - T&CS APPLY

VIEW TRIP

Italy : Sicily

Walking the Highlights of Western Sicily

£1129

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

Italy : Veneto

Walking in the Prosecco Hills

£779

NEW FOR 2025

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Self-guided walking

5 nights,
hotel-to-hotel

Level: 1+ & 2

Navigation App

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Italy : Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

£819

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

Holland

Cycling from Amsterdam

£839

NEW FOR 2025

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Self-guided cycling

3 nights,
single centre

Level: 1+
Leisurely plus

Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

France : Burgundy

Tour de France - Burgundy

£929

NEW FOR 2025

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Self-guided cycling

3 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

France : Provence

Tour de France - Provence

£949

NEW FOR 2025

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Self-guided cycling

3 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

Slovakia

Walking the Tatra Mountains in Slovakia

£959

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

Italy : Istria

Walking the Highlights of Istria: Italy, Slovenia & Croatia

£999

NEW FOR 2025

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

#250 SAVING - T&CS APPLY

VIEW TRIP

Germany : Bavaria

Walking the Black Forest to Lake Constance

£1049

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

Italy : Sardinia

Walking Sardinia's Green Coast

£1079

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

Italy : The Dolomites

Cross country skiing in the Dolomites

£1089

NEW FOR 2025

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Winter snow holiday

7 nights,
single centre



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Italy : Veneto

Adriatic Coast - Venice to Porec Ride

£1099

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

#250 SAVING - T&CS APPLY

VIEW TRIP

Bosnia

Walking the Olympic Mountains of Bosnia

£1189

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

#250 SAVING - T&CS APPLY

VIEW TRIP

Greece : Peloponnese

Peloponnese Coast and Mountain Walking

£1209

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

France : The Loire

Tour de France - Loire

£1279

NEW FOR 2025

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

Germany : The Moselle

Meandering the Moselle Cycle Path

£1349

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Optional
e-bike hire

£250 SAVING - T&CS APPLY

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France : The French Riviera

The French Riviera Golden Islands

£1379

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 1+
Leisurely plus

Printed route
directions

#250 SAVING - T&CS APPLY

VIEW TRIP

France : Canal du Midi

Tour de France - Canal du Midi

£1389

NEW FOR 2025

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Self-guided cycling

4 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

Norway

Cross Country Skiing at Rondane National Park

£1399

NEW FOR 2025

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Winter snow holiday

5 nights,
single centre



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Spain : Balearic Islands

Walking Mallorca trails and traditional Fincas

£1409

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

France : Alsace

Cycling the Scenic Rhine: Strasbourg to Mainz

£1419

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

£1459

NEW FOR 2025

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Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

Croatia

Hike, Bike & Paddle Croatia

£1479

NEW FOR 2025

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Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

Spain : Extremadura

Cycling Central Spain in Style

£1489

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

France : Atlantic Coast

Tour de France - Atlantic Coast

£1499

NEW FOR 2025

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2 & 2+

Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

France : Normandy

Paris to the Sea Along the Seine River

£1699

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

£250 SAVING - T&CS APPLY

VIEW TRIP

Denmark

Nordic Cities by Rail

£1829

NEW FOR 2025

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Self-guided cultural tour

9 nights,
hotel-to-hotel



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Morocco

Morocco: Mountains, Desert & Coast

£2179

NEW FOR 2025

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Self-guided cultural tour

7 nights,
hotel-to-hotel



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Iceland

Walking Iceland's Diamond Circle

£2299

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

Iceland

An Icelandic Adventure

£2479

NEW FOR 2025

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Self-guided cultural tour

7 nights,
hotel-to-hotel



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Japan

Japan: Hiroshima & Island Hopping

£3499

NEW FOR 2025

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Multi-activity holiday

10 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

£250 SAVING - T&CS APPLY

VIEW TRIP

Faroe Islands

Walking the Faroe Islands - With Private Guide

£3689

NEW FOR 2025

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Private guided walking

7 nights,
single centre

Level: 2+
Moderate plus

£250 SAVING - T&CS APPLY

VIEW TRIP

Japan

Exploring the land of Shogun and Samurai

£3879

NEW FOR 2025

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Self-guided cultural tour

10 nights,
hotel-to-hotel



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Peru

Walking Machu Picchu - With Private Guide

£4249

NEW FOR 2025

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Private guided walking

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

£250 SAVING - T&CS APPLY

VIEW TRIP

France

Tour de France

£5259

NEW FOR 2025

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Self-guided cycling

20 nights,
hotel-to-hotel

Level: 2 & 3

Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP
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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.