At Headwater we specialise in creating unique self-guided walking and cycling holidays. Beautiful landscapes, historic destinations and gastronomic cuisine are typical of our handcrafted itineraries.
Perhaps this is why we won the awards for Best Small Holiday Company to Western Europe, Iberia/Macronesia, and Italy at the British Travel Awards 2023.
We've collected our most popular holidays together in a single collection. These classic holidays encapsulate everything that makes Headwater special. Why not find out for yourself what makes an award-winning, bestselling trip and join us for your holiday in 2024?
Self-guided walking
7 nights,
twin centre
Level: 2
Moderate
Headwater
Navigation App
Self-guided walking
8 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
Self-guided walking
7 nights,
single centre
Level: 1+
Leisurely plus
Headwater
Navigation App
Self-guided walking
7 nights,
single centre
Level: 2+
Moderate plus
Headwater
Navigation App
Self-guided walking
7 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
Self-guided cycling
10 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Headwater
Navigation App
Self-guided walking
5 nights,
hotel-to-hotel
Level: 2
Moderate
Printed route
directions
Self-guided walking
5 nights,
hotel-to-hotel
Level: 2
Moderate
Printed route
directions
Self-guided walking
6 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Headwater
Navigation App
Self-guided walking
6 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Headwater
Navigation App
Self-guided walking
7 nights,
single centre
Level: 2
Moderate
Printed route
directions
Self-guided walking
5 nights,
hotel-to-hotel
Level: 2
Moderate
Printed route
directions
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Navigation App
Self-guided cycling
8 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
Self-guided walking
6 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Headwater
Navigation App
Self-guided walking
8 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
Self-guided cycling
6 nights,
hotel-to-hotel
Level: 1
Leisurely
Headwater
Navigation App
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
Self-guided walking
6 nights,
twin centre
Level: 2
Moderate
Printed route
directions
Guided group walking
7 nights,
single centre
Level: 1+
Leisurely plus
Printed route
directions
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Headwater
Navigation App
Self-guided cycling
6 nights,
hotel-to-hotel
Level: 3
Stretching
Headwater
Navigation App
Self-guided walking
7 nights,
single centre
Level: 2
Moderate
Headwater
Navigation App
Self-guided cycling
10 nights,
hotel-to-hotel
Level: 1
Leisurely
Headwater
Navigation App
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Headwater
Navigation App
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Headwater
Navigation App
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 1
Leisurely
Headwater
Navigation App
Self-guided walking
8 nights,
hotel-to-hotel
Level: 1
Leisurely
Printed route
directions
Self-guided walking
8 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
Self-guided pilgrimage
10 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.
