NEW Holidays for 2025

Showing 41 out of 338 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

£459

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

£569

NEW FOR 2025

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Self-guided walking

3 nights,
single centre

Level: 1+ & 2

Printed route
directions

United Kingdom : The Channel Islands

Walking in Jersey Premium

£629

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

£629

NEW FOR 2025

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Self-guided walking

7 nights,
single centre

Level: 1+
Leisurely plus

Headwater
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Slovenia

Walking in the Soča and Bohinj Valleys

£979

NEW FOR 2025

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Printed route
directions

Spain : The Canary Islands

Walking in Fuerteventura along the GR 131

£1039

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

£1089

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

Spain : The Canary Islands

Walking across La Gomera

£1239

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Italy : Italian Lakes

Walking at Lakes Orta and Maggiore

£1379

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

£1739

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

£1889

NEW FOR 2025

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Canada : Sunshine Coast

Walk & Paddle Canada’s Sunshine Coast

£2609

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

£999

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

£719

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

£759

NEW FOR 2025

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Self-guided cycling

3 nights,
single centre

Level: 1+
Leisurely plus

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France : Burgundy

Tour de France - Burgundy

£829

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

£849

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

£899

NEW FOR 2025

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Winter snow holiday

7 nights,
single centre

Italy : Sardinia

Walking Sardinia's Green Coast

£929

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Veneto

Adriatic Coast - Venice to Poreč Ride

£959

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

£999

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

£1069

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

£1089

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Greece : Peloponnese

Walking the Historical Paths of Outer Mani

£1149

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

£1179

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

£1179

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Croatia

Hike, Bike & Paddle Croatia

£1209

NEW FOR 2025

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Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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

Germany : Bavaria

Meandering the Moselle Cycle Path

£1249

NEW FOR 2025

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

France : Canal du Midi

Tour de France - Canal du Midi

£1289

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

£1359

NEW FOR 2025

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Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

Greece

Walking the Wonders of Crete

£1379

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Spain : Extremadura

Cycling Central Spain in Style

£1389

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

£1399

NEW FOR 2025

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2 & 2+

Navigation App

Denmark

Nordic Cities by Rail

£1699

NEW FOR 2025

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Self-guided cultural tour

9 nights,
hotel-to-hotel

Morocco

Morocco: Mountains, Desert & Coast

£2079

NEW FOR 2025

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Self-guided cultural tour

7 nights,
hotel-to-hotel

Iceland

Walking Iceland's Diamond Circle

£2199

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

£2379

NEW FOR 2025

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Self-guided cultural tour

7 nights,
hotel-to-hotel

Japan

Japan: Hiroshima & Island Hopping

£3399

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

£4149

NEW FOR 2025

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Private guided walking

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

£5159

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.