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Showing 22 out of 337 trips

Ireland

Dublin & The Wicklow Way Walking

£969

 
 

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Self-guided walking

5 nights,
hotel-to-hotel

Level: 2
Moderate

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Italy : The Dolomites

Walking the Dolomites of Alta Badia

£1479


4.8 (23 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
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Switzerland : Valais

Walking in Val D'Anniviers

£1549


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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Ireland

Walking the Kerry Way and Killarney N.P.

£1039


4.8 (4 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

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Portugal : The Algarve

Walk the Algarve's Wild West

£1049


4.8 (86 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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United Kingdom : Lake District

Literary Walking in the Lake District

£1399


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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Cyprus

WALKING THE AKAMAS PENINSULA

£619


4.5 (11 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 1 & 2

Headwater
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Ireland

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

£779


4.0 (1 reviews)

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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Italy : Liguria

Walking in the Cinque Terre and Portofino

£779


4.3 (7 reviews)

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Self-guided walking

6 nights,
single centre

Level: 2
Moderate

Navigation App

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France : Burgundy

Walking in Burgundy’s Vineyards - Short Break

£939

 
 

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Self-guided walking

4 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
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Austria : The Tyrol

Alpine Walks in the Stubai Valley

£969


4.6 (11 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
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Austria : The Tyrol

Walking the Tyrolean Mountains

£989


5.0 (1 reviews)

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Self-guided walking

6 nights,
single centre

Level: 2
Moderate

Headwater
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Switzerland : The Bernese Oberland

Walk the Crossroads of Five Passes

£1049


4.8 (5 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 3

Headwater
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Switzerland

Walking in the Lower Engadine

£1139


5.0 (2 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1 to 3

Printed route
directions

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France : Burgundy

Walking in Burgundy’s Vineyards

£1149


4.7 (6 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Greece : Peloponnese

Walking the Historical Paths of Outer Mani

£1189

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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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 : Mont Blanc

Mont Blanc Highlights

£1645

 
 

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Guided group walking

7 nights,
single centre

Level: 3
Stretching

Printed route
directions

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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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Spain : Catalonia

Catalonia Activities

£839


4.5 (13 reviews)

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Multi-activity holiday

7 nights,
single centre

Level: 1
Leisurely

Headwater
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Ireland

Walking and Cycling the Wild Atlantic Way

£1179

 
 

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Multi-activity holiday

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

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France : The Dordogne

Dordogne Activities

£1289


4.8 (31 reviews)

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Multi-activity holiday

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

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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.