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Cycling Holidays

Cycling Holidays

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Cycling is great for independent exploring as you can follow any route you choose using our 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 along French rural roads past pretty châteaux to coastal tracks and hidden coves on the beautiful Italian island of Sicily.

Travel across the UK, Ireland, Europe, and the Mediterranean on one of our cycling tours. You will cover greater distances travelling on two wheels than you would on two feet, leaving more time to reach those touchpoints and soak up more of the atmosphere, right from your saddle.

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Types of cycling holidays

Regardless of your experience or fitness level, there's a cycling holiday available for all abilities. Choose a self-guided cycling tour where you're free to explore at your own pace on our top-quality, custom-made bikes. For those who are new to cycling holidays and want to soak up the views and culture, our guided cycling tours are a great place to start.

To take some of the strain, you could choose to take it easy with our electric bike holidays. They keep you going that little bit longer on daunting hill climbs and long-distance rides. Take the opportunity to level up your usual routes using one of our top-of-the-line e-bikes.

View our full range of cycling holidays

Cycling holidays

Popular cycling destinations

Whether you want to jet off abroad or prefer a staycation, we offer cycling holidays to the world's most beautiful hidden gems. There's no better way to explore Europe than on two wheels and our cycling tours combine scenic views, culture, and history so you experience everything the continent has to offer.

Choose one of our cycling tours of Italy and enjoy the sun-soaked coastal trails and winding mountains before taking a dip in the Adriatic and sampling the famous cuisine. If green rolling hills, flowing rivers, and nature reserves sound more inviting, then our tours in Germany are for you. To explore quaint villages and natural beauty that's a little closer to home, our UK cycling tours are ideal.

We understand that not everyone is a world-class map reader so, on all our cycling holidays, we now offer our Headwater Navigation App. This provides turn-by-turn route directions via your smartphone for extra peace of mind. This includes detours to places of interest, shortcuts to avoid hills, and places to stop off for lunch!

Why choose Headwater for cycling tours?

We began in 1985 and now, with over 35 years of creating exciting holiday packages, we know just what you need from a cycling tour. Our itineraries are crafted so you can take advantage of the cultural gems and historical sites that all our cycling holiday destinations have to offer.

You can Book and Travel with Confidence when it comes to your cycling holiday with us. Our industry-leading booking protection gives you the financial security and flexibility you need when travelling abroad. This gives you that extra peace of mind when you book with us.

Please contact our friendly team if you have any questions about our award-winning cycling holidays. You can use our online form or give us a ring at 1-800-267-3347 and a member of our team will be happy to handle your query.

    Cycling holidays

    Overall customer rating, based on 1104 reviews

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.