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

CA$1075

NEW FOR 2025

VIEW TRIP

Self-guided walking

4 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

United Kingdom : The Channel Islands

Walking in Guernsey and Sark

CA$1285

NEW FOR 2025

VIEW TRIP

Self-guided walking

3 nights,
single centre

Level: 1+ & 2

Headwater
Navigation App

United Kingdom : The Channel Islands

Walking in Jersey Premium

CA$1400

NEW FOR 2025

VIEW TRIP

Self-guided walking

3 nights,
single centre

Level: 1+ & 2

Headwater
Navigation App

Gozo

Walking on Glorious Gozo

CA$1400

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
single centre

Level: 1+
Leisurely plus

Headwater
Navigation App

Spain : The Canary Islands

Walking in Fuerteventura along the GR 131

CA$2175

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Headwater
Navigation App

Albania

E-bike Across Southern Albania

CA$2270

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

Germany : Saxon Switzerland

Walking in the Elbe Sandstone Mountains

CA$2310

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Printed route
directions

Spain : The Canary Islands

Walking across La Gomera

CA$2555

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Italian Lakes

Walking at Lakes Orta and Maggiore

CA$2860

NEW FOR 2025

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Level: 1+ & 2

Headwater
Navigation App

France : Atlantic Coast

Cycling along the Atlantic Coast

CA$3505

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

Portugal : Mainland Portugal

Coimbra to Lisbon Cycling

CA$3790

NEW FOR 2025

VIEW TRIP

Self-guided cycling

11 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Canada : Sunshine Coast

Walk & Paddle Canada’s Sunshine Coast

CA$5160

NEW FOR 2025

VIEW TRIP

Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 1+ to 3

Headwater
Navigation App

Italy : Sicily

Walking the Highlights of Western Sicily

CA$2100

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

Italy : Tuscany

Treasures of Tuscany Walk: San Gimignano to Volterra

CA$1570

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

Holland

Cycling from Amsterdam

CA$1645

NEW FOR 2025

VIEW TRIP

Self-guided cycling

3 nights,
single centre

Level: 1+
Leisurely plus

Navigation App

France : Burgundy

Tour de France - Burgundy

CA$1780

NEW FOR 2025

VIEW TRIP

Self-guided cycling

3 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Navigation App

France : Provence

Tour de France - Provence

CA$1815

NEW FOR 2025

VIEW TRIP

Self-guided cycling

3 nights,
hotel-to-hotel

Level: 3
Stretching

Printed route
directions

Italy : The Dolomites

Cross country skiing in the Dolomites

CA$1910

NEW FOR 2025

VIEW TRIP

Winter snow holiday

7 nights,
single centre

Italy : Sardinia

Walking Sardinia's Green Coast

CA$1970

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Veneto

Adriatic Coast - Venice to Poreč Ride

CA$2025

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Germany : Bavaria

Walking the Black Forest to Lake Constance

CA$2100

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Spain : Balearic Islands

Walking Mallorca trails and traditional Fincas

CA$2235

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Bosnia

Walking the Olympic Mountains of Bosnia

CA$2270

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

France : The Loire

Tour de France - Loire

CA$2445

NEW FOR 2025

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

Spain : Andalucia

E-biking in Andalucia: Sierra de Aracena

CA$2445

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Norway : Gudbrandsdalen

Cross Country Skiing at Rondane National Park

CA$2445

NEW FOR 2025

VIEW TRIP

Winter snow holiday

5 nights,
single centre

Croatia

Hike, Bike & Paddle Croatia

CA$2500

NEW FOR 2025

VIEW TRIP

Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Germany : The Moselle

Meandering the Moselle Cycle Path

CA$200

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Navigation App

France : The French Riviera

The French Riviera Golden Islands

CA$2635

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 1+
Leisurely plus

Printed route
directions

France : Canal du Midi

Tour de France - Canal du Midi

CA$2650

NEW FOR 2025

VIEW TRIP

Self-guided cycling

4 nights,
hotel-to-hotel

Level: 3
Stretching

Navigation App

Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

CA$2785

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

Spain : Extremadura

Cycling Central Spain in Style

CA$2840

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

France : Atlantic Coast

Tour de France - Atlantic Coast

CA$2860

NEW FOR 2025

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2 & 2+

Navigation App

Greece

Walking the Wonders of Crete

CA$2935

NEW FOR 2025

VIEW TRIP

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

CA$3240

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Printed route
directions

Denmark

Nordic Cities by Rail

CA$3430

NEW FOR 2025

VIEW TRIP

Self-guided cultural tour

9 nights,
hotel-to-hotel

Morocco

Morocco: Mountains, Desert & Coast

CA$4155

NEW FOR 2025

VIEW TRIP

Self-guided cultural tour

7 nights,
hotel-to-hotel

Iceland

Walking Iceland's Diamond Circle

CA$4380

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1 to 3

Headwater
Navigation App

Iceland

An Icelandic Adventure

CA$4725

NEW FOR 2025

VIEW TRIP

Self-guided cultural tour

7 nights,
hotel-to-hotel

Japan

Japan: Hiroshima & Island Hopping

CA$6660

NEW FOR 2025

VIEW TRIP

Multi-activity holiday

10 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Peru

Walking Machu Picchu - With Private Guide

CA$8085

NEW FOR 2025

VIEW TRIP

Private guided walking

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

CA$10005

NEW FOR 2025

VIEW TRIP

Self-guided cycling

20 nights,
hotel-to-hotel

Level: 2 & 3

Navigation App

Tap here to filter results

Filter and sort

Holiday type
All

  • Self-guided walking
  • Self-guided cycling
  • Ski holidays
  • Canoeing
  • Multi activity
  • Pilgrimage
  • Private guided walking
  • Cultural tour
  • Guided group walking
  • Guided group cycling

Destination
All

  • Italy
  • Spain
  • France
  • Portugal
  • UK
  • Andorra
  • Austria
  • Belgium
  • Bermuda
  • Bosnia
  • Canada
  • Cape Verde
  • China
  • Croatia
  • Czechia
  • Denmark
  • Finland
  • Germany
  • Gozo
  • Holland
  • Ireland
  • Malta
  • Montenegro
  • Norway
  • Romania
  • Slovenia
  • Sweden
  • Switzerland
  • USA

Departure month
All

  • Jan
  • Feb
  • Mar
  • Apr
  • May
  • Jun
  • Jul
  • Aug
  • Sep
  • Oct
  • Nov
  • Dec

Activty level
All


  • Leisurely

  • Moderate

  • Demanding

  • Challenging

Accommodation type
All


  • Single centre

  • Twin centre  

  • Hotel-to-hotel

Best for
New holidays

  • Singles
  • Couples
  • Families
  • Food lovers
  • Wine lovers
  • Nature lovers
  • Bird watchers
  • Historic sites
  • Vegetarians
  • Swimming opportunities
  • Electric bikes
  • Tandem bikes
  • GPS navigation
  • Coastal routes
  • Island exploring
  • Lakes and rivers
  • High peaks
  • Unique accommodation
  • New holidays
  • Bestsellers

Sorted by


  • Price

  • Duration

  • Level

Update filters

 

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.