DISCOVER OUR AWARD-WINNING, BESTSELLING HOLIDAYS IN 2024

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?

  • Bestselling Walking Holidays
  • Bestselling Cycling Holidays

 

Slovenia

Julian Alps to the Adriatic Cycling

£1889


4.8 (118 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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Austria

Cycling from Vienna to Budapest

£1019


4.6 (49 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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France : The Dordogne

Dordogne Valleys & Villages Cycling

£1069


4.7 (42 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

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Spain : Catalonia

Contrasts of Catalunya Cycling

£1079


4.7 (53 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 1
Leisurely

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Spain : Balearic Islands

Cycling in Mallorca: Coast to Coast

£1179


4.7 (25 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

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Italy : Puglia

Contrasts of Puglia Cycling

£1279


4.6 (123 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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Spain : Andalucia

Cycling in Andalucia: Seville to Cadiz

£1349


4.3 (12 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 3
Stretching

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United Kingdom : Norfolk

Contrasts of Norfolk Cycling

£1379


5.0 (1 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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Austria : Carinthia

Lake Constance Cycling

£1389


4.7 (88 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1
Leisurely

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Portugal : Mainland Portugal

Porto Coastal Cycling

£1449


4.4 (59 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1
Leisurely

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Croatia

Coastal Croatia - Porec to Pula Cycling

£1479


4.7 (85 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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Italy : Piedmont

Gastronomic Barolo Cycling by e-bike

£2299


4.8 (88 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

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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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