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Cycling Holiday Through Fields

How to Plan a Cycling Holiday

From leisurely cyclists to keen peddlers, there's a cycling holiday best suited to you.

When researching how to plan a cycling holiday, it can be overwhelming at first, and you may not know where to start. That’s where Cycling for Softies comes in, with our holiday planning guide. We have over 40 years of experience in booking leisurely adventures on two wheels, so have plenty of tips and know-how. From choosing your holiday type to deciding your destination, we’ll tell you how to plan a cycling holiday so you can get the most out of your trip.

Cycling Through Flower Fields

Who’s Going?

The first step when wondering how to plan a cycling holiday is to finalise how many are going on the trip. Group size is an important factor, as some holiday types are better suited for larger groups than others. On our guided cycling holidays, groups have a maximum capacity of 8, so this may not be the best option for any party larger than this. Alternatively, single-centre holidays are often perfect for large groups. Staying at the same hotel throughout the trip, you’ll venture out each day to explore the surrounding region. This is wonderful as it means the party can split up and explore independently, meeting back at the hotel each evening.

For smaller groups, often a self-guided cycling holiday is our pick for you. If just a few of you are wondering how to plan a cycling holiday, then sticking together as a group every day is definitely the best plan of action. Not only this, but the smaller party size can make it easier to decide on a plan of action when navigating thanks to fewer voices pitching in. Cycle along quiet country lanes together, stop off at ancient winemaking towns and dining together at gourmet restaurants.

Another factor to note when looking at how to plan a cycling holiday is whether children are coming too. A family cycle trip is a fantastic way to experience a region together; the younger ones are enthralled by local folk tales, and parents can both enjoy a delicious glass of wine from the vineyards. Single centre holidays are also a great choice for families, as you can get yourselves all settled in, without moving accommodation each night.

Cycling Holidays Down Country Lanes

Cycling Experience

The cycling experience of the group is something else to consider. Beginner cyclists may prefer more gentle routes. Our cycling holidays cater for all levels of ability, so everyone can enjoy a leisurely cycling experience. However, some regions are more suited to beginners/keen cyclists than others. The Loire Valley is our first choice for any beginner cyclist looking for a holiday. Almost entirely flat with canal-side routes, this is a strong choice for beginners wondering how to plan a cycling holiday. More keen cyclists may look towards Provence and Tuscany, where rugged hills reveal gorgeous views and hilltop towns.

Ultimately, the use of an e-bike can make any tour feel leisurely. Save up power for that big hill, and zoom to the top without ever breaking a sweat. For those who perhaps aren’t as mobile as they used to be, an e-bike is a wonderful way to experience the rush and freedom that cycling in their youth provided.

E-Bike Cycling Holidays

What Do You Want to See?

Another important factor in knowing how to plan a cycling holiday is deciding what you want to see. For many, a holiday is all about experiencing the culture and history of a region as you immerse yourself in their way of life. If this is an important part of your holiday, then our Umbria cycling tours are a great choice. The Umbrian culture can be felt everywhere you visit, and it’s even baked right into their food. In no other region of Italy will you find more inviting and authentic people.

Another important part of a holiday for some is the exploration of beautiful landscapes filled with flora and fauna. Our Provence cycling holidays are perfect for just that. Venture into the stunning Camargue National Park, famed for its unique ecosystems and wildlife. Cycle past herds of wild white horses as well as vibrant flamingos all flocking together. So, if you’re trying to work out how to plan a cycling holiday with nature lovers, then Provence should definitely be on your mind.

If you’re a foodie like us, then Emilia Romagna is a fantastic choice for your holiday. So many beloved dishes known the world over have their origins here; from Bolognese to Parma ham, there are so many specialities here. Food lovers are well taken care of in Emilia Romagna – something to remember next time you wonder how to plan a cycling holiday with a foodie.

For wine lovers, Champagne is the undisputed queen of wines. Famed for its elegance and luxury, the bubbling gold drink has long been associated with celebrations and prestigious events. A cycling holiday in Champagne is the perfect opportunity to visit world-famous vineyards and taste the amber gold wine for yourself. Wine is an almost sacred aspect of dining to many, so a trip to Champagne can almost be seen as a pilgrimage.

Champagne Wine Lovers


Finally, the time of year you’re planning to go on a cycling holiday is important. Some regions can vary hugely throughout the year. For example, spring in the Cotswolds means the countryside will be in full bloom, with wildflower meadows and cottage gardens showcasing a kaleidoscope of colours. In the autumn, the colours dramatically shift to oranges, yellows and reds as the leaves turn, changing the atmosphere of the region along with it.

Different regions also shine brighter than others at different times of the year. In late summer, the Tuscan hills are set ablaze with gorgeous sunsets on warm evenings. Tuscany is one of our favourite regions to recommend to those asking how to plan a cycling holiday. There’s so much to see and do when exploring this Italian heartland.

Cotswolds Idyllic Houses

For more information on how to plan a cycling holiday, call our cycling experts today on 020 7471 7760.

We Can Tailor-make
a Holiday to Suit You…

We have a team of experts on hand to help you choose the perfect holiday. From a luxury cycling holiday weekend in Tuscany to a big adventure in through the Loire Valley, we’re whatever you want your holiday to be.