Family Holidays - Cycling, Walking & Multi Activity

Showing 44 out of 329 trips

Time spent on holiday is invaluable for families to bond and enjoy each other's company away from the stresses and rigours of everyday life. The following Headwater holidays are perfect for families with older children (over 12). Our walking or cycling holidays are sure to keep the kids active and entertained throughout the duration of your holiday

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Denmark

Cycling from Copenhagen

£1019


5.0 (1 reviews)

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Self-guided cycling

4 nights,
single centre

Level: 1
Leisurely

Headwater
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Belgium

Cycling from Bruges to Amsterdam

£1519


4.0 (1 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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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

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Canada : Prince Edward Island

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
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Italy : Veneto

Heart of Veneto Cycling

£1039


4.8 (72 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

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Switzerland : Davos

Walking in Val D'Anniviers

£1649


5.0 (1 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 3

Printed route
directions

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United Kingdom : Dorset

Literary Walking in the Lake District

£989


4.8 (32 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Ireland

Walking the Kerry Way and Killarney N.P.

£1139


4.8 (5 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

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Austria : Salzburg

Austrian Lakes Activities

£1169


4.8 (68 reviews)

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Multi-activity holiday

7 nights,
single centre

Level: 1
Leisurely

Headwater
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Portugal : The Algarve

Walk the Algarve's Wild West

£1179


4.8 (89 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Austria : Lake Constance

Lake Constance Cycling

£1489


4.7 (88 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
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Croatia

Coastal Croatia - Porec to Pula Cycling

£1539


4.7 (85 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Cyprus

Walking the Akamas Peninsula

£759


4.5 (11 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 1 & 2

Headwater
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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

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Spain : Catalonia

Catalonia Activities

£859


4.5 (13 reviews)

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Multi-activity holiday

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

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Ireland

Walking the Kerry Way and Killarney N.P. - Short Break

£879


4.0 (1 reviews)

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

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Switzerland : The Bernese Oberland

Cross country skiing in Kandersteg - Short Break

£919


4.8 (4 reviews)

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Winter snow holiday

5 nights,
single centre



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France : Burgundy

Walking in Burgundy's Vineyards - Short Break

£1039

 
 

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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Austria : The Danube

Cycling along the Danube from Passau to Vienna

£1049


4.9 (20 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

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Sweden : sweden

Cycling from Stockholm

£1059

 
 

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Self-guided cycling

5 nights,
single centre

Level: 1+
Leisurely plus

Headwater
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France : The French Riviera

Multi Activity in the Loire

£1059

 
 

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Multi-activity holiday

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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Austria : The Tyrol

Alpine Walks in the Stubai Valley

£1069


4.6 (11 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
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Austria : Salzburg

Walking the Tyrolean Mountains

£1089


5.0 (1 reviews)

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Self-guided walking

6 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

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Switzerland : Davos

Walk the Crossroads of Five Passes

£1149


4.8 (5 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 3

Headwater
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Austria : Lake Constance

Highlights of Lake Constance by bike

£1159


4.9 (27 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
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Switzerland

Cross country skiing in Kandersteg

£1169


4.7 (6 reviews)

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Winter snow holiday

7 nights,
single centre



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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
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France : The Loire

Canoeing on the Loire

£1279

 
 

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5 nights,
hotel-to-hotel

Navigation App



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Ireland

Walking and Cycling the Wild Atlantic Way

£1279

 
 

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Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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France : Burgundy

Walking in Burgundy's Vineyards

£1279


4.8 (8 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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France : The Dordogne

Canoeing on the Dordogne

£1299


4.9 (55 reviews)

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8 nights,
hotel-to-hotel

Printed route
directions



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France : Canal du Midi

Canal du midi Cycling : from Toulouse to Sete

£1319


4.7 (3 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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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

Navigation App

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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

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Sweden : sweden

Cycling Stockholm's Archipelago

£1389


5.0 (1 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

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France : The Dordogne

Dordogne Activities

£1389


4.8 (31 reviews)

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Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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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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France

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

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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

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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

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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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France : Mont Blanc

Mont Blanc Highlights

£1345

 
 

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Guided group walking

7 nights,
single centre

Level: 3
Stretching

Printed route
directions

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Croatia

Cycling Croatia's Dalmatian Coast

£1545

 
 

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Guided group cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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Morocco

Highlights of Morocco - In Comfort

£1549

 
 

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Guided group walking

14 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

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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.