Cycling Holidays

Self Guided Cycling Holidays

Explore at your own pace with Headwater

On a self-guided cycling tour, you're in control. So, whether it's a long lunch or a visit to an ancient chateau, you make the call. To help you choose a cycling holiday that best suits your level of fitness, we provide four different journey grades.

You can either move between hotels, enjoying our routes which will take you from A to B, meanwhile we take care of moving your luggage to your next hotel. Simply leave your bags packed in the morning and they'll be waiting for you at your next hotel at the end of the afternoon. On your rest days, spend them exploring the local area or unwind by the pool, it is up to you - it is your holiday after all. Alternatively, you can book a single-centre cycling holiday and enjoy a collection of routes taking you out, around and back to your chosen hotel.

Whichever you choose, you'll cycle at your own pace and have plenty of opportunities for detours to see places of interest en-route.

View our self-guided cycling holidays

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Where can I go on my independent cycling holiday?

At Headwater, we're proud to offer an array of top destinations from which to start your self-guided cycling tour. We provide an inspirational selection, with some tours starting in one country and finishing in another. A handful of our favourite destinations include:

The Danube River

Dreaming of cruising down the Danube? We offer a selection of self-guided cycling tours that traverse some of the most iconic cities in Europe. The final destination will be your choice: you can either start in Passau and end in Vienna or head from Vienna to Budapest, the capital of Hungary. Architecture, thick deciduous forests, and steady rolling landscapes await you on our self-guided Danube cycling holidays. Explore the Danube »


From the picturesque vineyards of the Champagne region to the quaint, dreamlike vistas of the Loire Valley, our independent cycling holidays in France promise an exceptional way to see this breathtaking country. Ride steadily between rolling pastures or conquer more challenging terrain in the hilltop villages of Provence. Discover France »

Great Britain

Going on an independent cycling holiday doesn't have to mean leaving the UK. We offer a fantastic selection of organised tours starting from selected locations in England, Wales and the rugged Scottish Highlands. Our cycling tours in Britain combine superior accommodation and on-hand support with the opportunity to discover new and exciting places. See what makes Britain great »


Italy has a certain kind of magic. When you go there on a self-guided cycling tour, you can discover the best the country has to offer. Our cycling holidays in Italy take you through some of the most famous valleys, coastlines, orchards and unspoilt villages, all with our first-class directions and on-demand support.Cycling in Italy »


For every type of cyclist, Spain is a bucket-list destination. Beaming sunshine, crystal clear waters and a rich cultural atmosphere make the country so special - not forgetting the beautiful scenery on quiet, winding roads through the hills. Our cycling tours in Spain take you through some of the most memorable and iconic cities, monuments, coastlines and contrasts. Head to Spain »

Why choose Headwater for a self-guided cycling tour?

You are in expert hands, so booking an independent cycling holiday with us will be a breeze. With over 35 years of experience behind us, we know a thing or two about providing memorable cycling trips from start to finish. We take the time to ensure that no matter where you'd like to go for your self-guided bike trips, you can make the most of each moment.

What's more, there are plenty of handy perks to benefit from when you book with us:

  • We're ATOL and ABTA-protected - You can relax in the knowledge that your booking comes with no risk. Find out more about your key rights when booking with us.
  • We can sort out your flight - You choose the best airport for you and we'll happily arrange the flights for your self-guided cycling tour.
  • Tailor-made for you - We can add pre or post stays to your cycling holiday to make your perfect trip.
  • Navigation App - We provide a fantastic navigation App to guide you through every turn with audio cues to make it even easier.
  • Award-winning tours - We run award-winning cycling holidays, as voted for by our valued customers in the prestigious British Travel Awards.
  • Top destinations - We offer over 100 cycling holidays in over 16 countries, so have a plethora of choice.
  • We're trusted - We've earned great reviews on Feefo from our customers thanks to the care we give to every booking.
  • We're climate-conscious - We're aiming for all our self-guided cycling tours to be Nature Net Positive; meaning we want our trips to have a positive impact on the environment.
  • We support local communities - Through the Exodus Travels Foundation, we help communities around the world access conservation, social and disaster relief projects.

Frequently asked questions

How does an independent cycling holiday start?

In most cases our trusted local partners will meet you and fit you out with bikes sized to suit you based on the heights you provide when you make the booking. Each one is supplied with a puncture repair kit alongside a few handy extras.
Where this happens, we'll also give you a briefing and be on hand to answer any questions you have. They will go through the route directions – firstly to point out any last-minute alterations and also to provide advice on things to do and places to visit.

How will I navigate on my cycling trip?

Many of our self-guided cycling holidays offer the Headwater Navigation App. It's an easy-to-use GPS App that provides turn-by-turn route directions with audio cues when cycling. Even if you have no map-reading experience or struggle to follow directions, we assure you our App will make it very easy.
Thanks to the audio cues you will have less need to stop and start whilst pedalling; you are left with more freedom to soak up your surroundings and enjoy the ride. We've also included 'points of interest' along the routes to highlight the amazing scenery, fascinating architecture and quaint little villages that make Headwater cycling holidays so special.
Find out about the Headwater navigation app

What sort of bike will I get?

The bikes on our self-guided cycling holidays are provided by our carefully selected local agent partners and as such the exact make and model of the bikes will vary by destination. However, each has been selected by our Programme Managers in order to provide you with the best option for the terrain and activity level of the chosen holiday. All of our bikes come equipped with a puncture repair kit in case you're unlucky enough to get a flat and each one is fitted with panniers for your picnic and sun cream.

Can I use an e-bike on my self-guided cycling holiday?

We now offer e-bikes as an option on many of our self-guided cycling holidays.
They provide all the benefits of a normal bike: you can enjoy gentle exercise, fresh open air, interaction with nature, and the chance to meet other cyclists. The difference is that you won't need any prior endurance cycling experience - and they have the bonus of making light work of the occasional uphill section! E-bikes are the perfect solution for those who'd like to share holiday experiences but don't necessarily share the same levels of fitness.
Find out more about our electric bikes

How do I plan my own cycling tour?

Planning a cycling tour involves a lot of logistics. From organising your initial travel documents to booking the right accommodation, there's a lot to think about. Add to that the creation of your own itinerary and the whole process might start to feel overwhelming.
When you book a self-guided bike tour with Headwater, all you need to do is choose a location that suits you and we'll do the rest. We organise everything from the airport transfer to your breakfast, so you can spend more time out on the bikes.

How many miles a day should you ride on a bike tour?

When you book one of our self-guided cycling holidays moving from hotel to hotel, our experienced team will advise you on the activity level to ensure it is an enjoyable holiday and you can take in the scenic routes on offer and relax on the rest days in between.
Where you are staying in a single hotel there's no pressure to go far. We'll provide you with routes to help you find the best spots – but there's no commitment to ride if you don't want to. Many of our guests only do a few miles each day, while others head out for longer adventures.

What is good to wear on a self-guided cycling holiday?

Deciding what to pack on a self-guided cycling holiday can be tricky, but the most important thing is to be as comfortable as possible. Check the weather forecast in advance to give yourself an idea of the conditions you might expect. Don't forget that the weather might be slightly unpredictable if you're heading to the mountains!
Make sure you pack at least a few pairs of cycling shorts, t-shirts and anything you feel good cycling in. You'll probably get quite warm too, so make sure you've got enough kit to last for the whole trip. Thanks to our dedicated luggage delivery from one hotel to the next, you won't need to worry about what you put in your bags.

Do I need to bring a helmet on a self-guided cycling holiday?

Besides your kit, the most important thing to pack is a bicycle helmet. Not only are helmets essential for your safety, but it's also a legal requirement for all cyclists to wear one in countries including Spain and Portugal.
Headwater believes that all cyclists should wear helmets in the interests of personal safety, although we accept that some customers will want to exercise their own choice in this matter. However, please do note that not wearing a helmet may affect the validity of your insurance. Those who decide not to wear a helmet do so entirely at their own risk.
If wishing to use a helmet you must bring your own with you as they are not available for hire.

What do I need to take on a self-guided cycling holiday?

Along with comfortable clothing, a sense of adventure and an appetite for fun, there are a few other items you may wish to bring if you have specific preferences on the bike. However, please do advise us in advance if you are planning to bring any of these so we can be prepared to help you fit them, such as:

  • Pedals
  • Cycling computers
  • Saddles
  • Water bottles
  • Bottle cages or hydration systems
  • Bike bags, including bar bags
  • Child seats