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Headwater Walking Late Getaways

Do you have the sudden urge to walk through majestic mountain trails, hushed forests, terraced vineyards, or coastal paths in the UK and further afield? With Headwater’s collection of late getaways, your next walking holiday could be sooner than you think! Browse our top trips below for inspiration.

 

Malta + Gozo

Highlights of Secrets of Malta Walking

£609


4.5 (2 reviews)

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Self-guided walking

4 nights,
single centre

Level: 2
Moderate

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Malta + Gozo

Discovering the Maltese Islands

£839


4.3 (10 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
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£250 SAVING - T&CS APPLY

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Spain : The Canary Islands

Walking the trails of Tenerife

£879


4.5 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2 & 3

Headwater
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Spain : The Canary Islands

Contrasts of Lanzarote

£1039


5.0 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
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Italy : The Bay of Naples

The Islands of Amalfi Walk

£1109


4.6 (14 reviews)

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Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

£250 SAVING - T&CS APPLY

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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
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£250 SAVING - T&CS APPLY

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Malta + Gozo

Walking on Gozo - Calypso's Isle

£869


4.6 (143 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1+
Leisurely plus

Headwater
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£250 SAVING - T&CS APPLY

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Italy : The Bay of Naples

Paths of the Amalfi Coast

£829


4.6 (28 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
Navigation App

£250 SAVING - T&CS APPLY

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Bermuda

Islands of Bermuda Walk

£1409


4.6 (38 reviews)

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Self-guided walking

7 nights,
single centre

Level: 1
Leisurely

Headwater
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#250 SAVING - T&CS APPLY

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Portugal : The Algarve

Walk the Algarve's Wild West

£1179


4.8 (90 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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£250 SAVING - T&CS APPLY

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United Kingdom : Wales

Highlights of the Pembrokeshire Coast

£1289


3.9 (8 reviews)

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Self-guided walking

6 nights,
twin centre

Level: 2
Moderate

Printed route
directions

£250 SAVING - T&CS APPLY

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Portugal : Mainland Portugal

Walking the Green Coast of Minho

£589


4.0 (1 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Printed route
directions

£250 SAVING - T&CS APPLY

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Portugal : Mainland Portugal

Walking the Mountains, Valleys & Coast of Minho

£759


5.0 (1 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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#250 SAVING - T&CS APPLY

VIEW TRIP

Malta + Gozo : Malta

Secrets of Malta Walking

£789


5.0 (4 reviews)

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Self-guided walking

7 nights,
single centre

Level: 2
Moderate

Headwater
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£250 SAVING - T&CS APPLY

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Spain : Andalucia

Walking the White Villages of the Alpujarras

£829


4.6 (7 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2 & 2+

Headwater
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£250 SAVING - T&CS APPLY

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United Kingdom : Dorset

Jewels of the Jurassic Coast Walk

£849


4.3 (3 reviews)

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Self-guided walking

6 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

United Kingdom : Wales

North Pembrokeshire Coast Walk

£1049

 
 

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Self-guided walking

6 nights,
twin centre

Level: 2+ & 3

Printed route
directions

£250 SAVING - T&CS APPLY

VIEW TRIP

United Kingdom : Wales

Highlights of the Gower Peninsula Walk

£1109


5.0 (2 reviews)

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Self-guided walking

5 nights,
twin centre

Level: 1+
Leisurely plus

Headwater
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£250 SAVING - T&CS APPLY

VIEW TRIP

Portugal : Mainland Portugal

Walk the Highlights of Northern Portugal

£1369


4.5 (6 reviews)

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Self-guided walking

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
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#250 SAVING - T&CS APPLY

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United Kingdom : Wales

Walking Offa's Dyke Path (North)

£1629

 
 

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Self-guided walking

9 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

£250 SAVING - T&CS APPLY

VIEW TRIP

Cape Verde

Cape Verde's Northern Islands - With Private Guide

£1699


4.9 (7 reviews)

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Private guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

£250 SAVING - T&CS APPLY

VIEW TRIP

Portugal : The Algarve

Walking the Algarve's South West

£1789


4.8 (33 reviews)

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Self-guided walking

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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.

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