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Cycling Holidays

Cycling Holidays

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Cycling gives great scope for independent exploring, as you can follow any route you choose using our comprehensive route directions, GPS route navigation and detailed maps.

Our suggested routes use quiet country lanes, and go by the places we think are most interesting – from cycling in France along rural roads past pretty châteaux to coastal tracks and hidden coves on the beautiful island of Sicily.

Travel across the UK, Ireland, Europe and the Mediterranean –you will cover more distance travelling on two wheels than you would on foot, leaving more time to reach those touchpoints and soak up more of the atmosphere, right from your saddle.

Watch our cycling holidays video

Explore at your own pace

On a self-guided cycling holiday you're free to explore at your own pace. So, whether it's a long lazy lunch or a quick detour to an ancient château, the choice is yours!

We provide you with top-quality custom-made bikes and our local representatives move your luggage for you from hotel-to-hotel as part of the package.

View our full range of cycling holidays

Cycling holidays

Take it easy with an electric bike

Well-designed and easy to use, an electric bike can help take the edge off daunting hill climbs, long distances and the occasional head wind! Emission-free, they keep you going for that little bit longer.

Having power assistance means you will be able to comfortably cycle further too (if you wish), meaning more places are within visiting distance. If you usually opt for our more gentle routes, you can now choose something a little more undulating with an e-bike as the effort required is similar.

Learn about our electric bikes

Electric bikes

You won't get lost with Headwater

We understand that not everyone is a world-class map reader so, on all our cycling holidays, we now offer our our Headwater Navigation App to give you turn-by-turn route directions via your smart phone. We also include detours to places of interest, shortcuts to avoid hills, and places to stop off for lunch!

Learn about our maps and notes

Our maps and notes

    Cycling holidays

    Overall customer rating, based on 1119 reviews

Frequently asked questions

What makes your cycling holidays special?

You get a very different view of things with Headwater. Travelling by bike, at your own pace, there's time to notice things you would miss from a car. You'll get to know the place you've chosen intimately and absorb the sights, the scents, and the atmosphere, in a way that you never could on an ordinary holiday. Cycling gives the most scope for independent exploring, as you can follow any route you choose using our maps and notes. Explore the heart of the country, in your own way and at your own pace, to discover the curiosities and splendours that make our holidays so interesting and so diverse.

Do I need to be a regular cyclist?

No not at all! All our cycling holidays are graded, starting off with just enough exercise to work up an appetite for the next great meal. There are longer route options if you're feeling energetic and, with our fully trained reps in each cycling area, there's always help available if you need it.

How will I move my luggage around?

The simple answer is - you won't need to! Our resident reps will collect your luggage each morning just after you leave your hotel and transport it to your destination, so your bags will always be waiting for you each evening. What's more, with certain holidays, they'll even collect your wine purchases for you too.

How are the routes planned?

Our routes are meticulously planned to ensure they are using quieter roads and tracks and go to places we think are particularly interesting. There are route options for avoiding hills, and suggestions for detours and off-road exploration. All this information is included in the detailed route notes that you'll receive in your pre-holiday documents. Why not download a sample copy to see?

How do we know which cycle is the right level for us?

To help you choose a holiday that best suits your level of fitness our cycling holidays are graded using our 'bike' system . On the individual holiday webpages (and in our brochure) you'll see that we've marked each tour from Level 1 to 4 so that you know what level of activities to expect.
Level 1: These holidays follow mainly flat, gentle routes with hardly any hills. The time you'll spend cycling is typically 2-4hrs, every other day. These holidays are a good choice for first timers, families with children, or those who haven't been on a bike in years! Longer route options available for the more energetic.
Level 2: These holidays offer more varied cycling, often on the flat, but with the occasional hilly section en route. You'll typically spend 3-5hrs cycling every other day. You don't need to be a regular cyclist or especially fit but, in hot weather, be prepared to start early and take it easy.
Level 3: Longer, more challenging routes better suited to regular cyclists. No special technical skills are required but you must be reasonably fit and confident in your cycling ability.
Level 2: Challenging trips that require confidence in your ability and physical condition. They are equivalent to an extended period of cycling at home. Previous mountain biking experience is essential for off-road trips, as they will involve some technical riding.

Can you tell me more about your bikes?

All our bikes are cleaned and maintained by our overseas agents, so we don't expect any problems. If anything does go wrong they'll come out to your hotel to fix it. Straight handlebars (not racing bike drop-handlebars), 21 gears, Mudguards, Pannier rack, Gel saddles, a set of panniers, a puncture repair kit & tyre levers, a pump, a lock, a phone holder and a Headwater bike briefing.