Pedal the Possibilities

After an incredible year full of interest-packed, self-guided holidays, award wins and 5-star client feedback, we’re thrilled to say that our team have been working hard behind the scenes to introduce a selection of brand new and unique hand-crafted cycling itineraries for next year. The possibilities are endless on a Headwater cycling holiday. Exploring places on two wheels allows you to go further, faster, giving you ample opportunities to extend your time discovering places that interest you.

Our relaxed routes are designed to be stress-free, with meticulous turn-by-turn directions– the audio navigation individually created for every one of our cycling itineraries. Enjoy your cycling holiday, map-free, whether you choose to cycle past lavender fields in the Cotes du Ventoux , ride along the iconic canal district on our Amsterdam to Brussels trip or pedal along cycle paths in County Kerry on the spectacular Wild Atlantic Way . If you think you'll be weighed down with luggage, think again - your belongings will be transported ahead for you so you can cycle at your own pace.

So, why not take the opportunity to browse through our collection of self-guided and guided cycling trips that are designed to immerse you into the destination’s local culture, or find inspiration by reading our blog .


Why choose Headwater?

 

Portugal : The Algarve

Cycling in The Real Algarve

£1419


4.7 (66 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Italy : Sicily

Cycling through Baroque Sicily

£1589


4.5 (22 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Slovenia

Julian Alps to the Adriatic Cycling

£2229


4.8 (123 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Austria : Lake Constance

Lake Constance Cycling

£1489


4.7 (91 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
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France : The Loire

Cycling The UNESCO Loire Valley

£1069


5.0 (3 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

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Spain : Catalonia

Classic Catalan Cycling

£1249


4.8 (12 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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France : Bordeaux

Cycling The Grand Crus of Bordeaux

£1289


4.5 (4 reviews)

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Self-guided cycling

5 nights,
hotel-to-hotel

Level: 2
Moderate

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Ireland : County Wicklow

Unspoilt Ring of Kerry Cycling

£1329


4.4 (5 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Austria : The Danube

Passau to Vienna Cycling

£1399


4.8 (76 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1
Leisurely

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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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