Cycling Holidays

Some say, there's nothing more freeing than discovering the world on two wheels. It's just you, your bike and the open road. And thanks to our user-friendly Headwater Navigation App, you can ride seamlessly from A to B using our easy-to-follow turn-by-turn instructions, making sure you never veer off the cycling path - unless you want to! You can even choose to travel by e-bike on a selection of our trips, which help to make lighter work of longer rides.

So, in 2024, why not take on a new cycling route in Scandinavia, riding through nature reserves and fishing villages from Stockholm to Copenhagen? Or cycle towards medieval towns and fairytale chateaux while pedalling in the Dordogne. If you're looking for panoramic views of golden beaches and quaint fishing villages steeped in maritime history, try our Cycling in the Real Algarve holiday.


Why choose Headwater?

New cycling holidays for 2024


Types of cycling holidays

Frequently asked questions

What makes your cycling holidays special?

Travelling by bike on one of our cycling tours gives you time to notice things you would miss in a car. You'll really get to know the place you've chosen by absorbing the sights, the scents, and the atmosphere, in a way that you never could on an ordinary holiday.
Cycling provides the largest scope for independent exploring. Entirely at your own pace, you can follow any route you choose using our maps and notes. Cycle the heart of the country in your own way to discover the curiosities and cultural sites that make our cycling holidays so interesting and so diverse.

Do I need to be a regular cyclist to participate in a cycling holiday?

No, not at all! All our cycling holidays are graded, starting with just enough exercise to work up an appetite before kicking it up a notch. There are longer route options if you're feeling ambitious 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?

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 bike holidays, they'll even collect your wine purchases for you too!

How are the routes planned?

Our routes are planned to ensure they use quieter roads and tracks that lead to the places we think are well worth the journey. There are route options for avoiding hills, and suggestions for detours and off-road exploration, so you can tailor any of our cycling tours to your requirements.
All this information is included in the detailed route notes that you'll receive in your pre-holiday documents.

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

All our cycling holidays are graded using our 'bike' system to help you choose a holiday that best suits your level of fitness. On the individual holiday web pages and brochures, all cycling holidays are marked from level 1 to 4 so that you know what level of activities to expect.
Level 1: These bike holidays follow mainly flat, gentle routes with hardly any hills. 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 are available for the more energetic.
Level 2: These cycling tours offer more varied cycling, often on the flat but with the occasional hilly section en route. You'll typically spend 3-5 hours 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.
Level 3: These longer, more challenging routes are better suited to regular cyclists. No special technical skills are required but you must be reasonably fit and confident in your cycling ability.
Level 4: These challenging cycling tours require confidence in your ability and physical condition and are equivalent to an extended period of cycling at home. Previous mountain biking experience is essential for off-road trips as they involve technical riding.

What bikes are used on your cycling holidays?

All our bikes are cleaned and maintained by our overseas agents so you can be confident that you're in safe hands. If anything does go wrong, they'll come out to your hotel to fix it. The bikes used on our cycling holidays have:
• 21 gears
• Straight handlebars
• Mudguards
• Pannier rack
• Gel saddles
• A set of panniers
• Puncture repair kit & tyre levers
• A pump
• A lock
• Phone holder
• Headwater bike briefing

What to pack for a cycling holiday?

We strongly advise that all cyclists bring appropriate footwear and clothing on our cycling holidays to make your trip as enjoyable as possible. Water bottles and sun cream are strongly recommended, especially in our hotter destinations.
Please note that cycling helmets are mandatory in Spain for all cyclists under 16, in Austria for children under 12 years, in Slovenia for children under 15 years, and in Croatia for children under 16 years. Each country has its own regulations. You are expected to bring your own helmet as we can't guarantee the availability of helmets to hire or purchase at your destination.
Even in countries where cycling helmets are not a legal requirement, we strongly recommend all customers wear them. Headwater will not be responsible for any issues with helmets or other protective headwear and not wearing one may affect the validity of your travel insurance.

How to plan for a cycling holiday?

All our cycling holidays can be tailor-made to your requirements, whether that includes combining trips, adding extra nights to your stay, or arranging travel from airports. Our packages can include flights and train services, but you can book your own travel if you prefer. All our accommodations have been inspected by the authorities of the country concerned.
To make sure you pick a holiday that best suits your level of fitness, we've rated all our cycling holidays clearly from 1-4 and marked those with a '+' that may have more challenging sections.

Do I need insurance for a cycling holiday?

It is a condition when booking one of our cycling holidays that you are insured. As our holidays are physically active, you must take our personal insurance or arrange a policy that has the equivalent cover and no exclusions.
Please see our travel insurance requirements for more information or call our sales team if you have any further questions.