Planning your first cycling holiday? Congratulations! You’ve officially entered the wonderful world of questionable tan lines, mid-ride coffee stops and post-ride beers that taste like you’ve won the Tour de France. It’s an adventure like no other and whether you’re daydreaming about breezy flat roads or bracing mountain climbs, one thing’s for sure: the excitement is real. So is the potential for a few rookie mistakes.

But fear not! With a bit of preparation and the right mindset, your first cycling holiday can be an unforgettable blend of scenic rides, camaraderie and well-earned indulgences (yes, we’re looking at you, post-ride gelato). This guide will walk you through the essentials: from picking the perfect destination to packing the right gear and planning your daily routes. Along the way, we’ll share tips, tricks and a few laughs to ensure your holiday is as smooth as your favourite road bike’s shifting.

Ready to trade your office chair for a saddle and your usual commute for rolling hills? Let’s dive in and turn your cycling holiday dreams into reality — without the unnecessary drama of a forgotten tyre pump or a wildly ambitious route.

Ready to trade your office chair for a saddle?

Choosing the Right Destination

When it comes to cycling holidays, choosing the right destination is like picking the perfect gear on a steep climb — it can make or break your experience. The beauty of Europe lies in its diversity, offering routes that cater to every fitness level and style of riding. But before you start fantasising about sunlit vineyards or towering mountain passes, let’s talk about a few key factors to consider.

Terrain: Know Your Limits (and Your Legs)
Are you dreaming of long, leisurely rides along river valleys, or do you secretly fancy yourself a Tour de France contender? For beginners and those who prefer a more relaxed pace, flat routes like those in the Loire Valley or along the Danube River are ideal. They’re scenic, forgiving and give you plenty of time to admire the view (and not just the wheel in front of you).

If you’re feeling a bit more adventurous — or maybe just slightly masochistic—mountainous regions like Switzerland or the Pyrenees offer breathtaking climbs and equally stunning descents. But be honest with yourself: no one wants to be the person pushing their bike up Mont Ventoux while others zoom past with a cheerful “Bon courage!”

Climate: Pack for Sunshine, Not Survival
There’s nothing worse than planning a dream holiday only to find yourself battling gale-force winds or torrential rain. Do a bit of homework and choose a destination with favourable weather during your trip. Andalucia, for instance, offers almost year-round sunshine, while Tuscany’s mild springs and autumns make it a cyclist’s dream. Meanwhile, Switzerland’s alpine passes are best tackled in summer unless you fancy riding through snow (spoiler: you don’t).

Accessibility: Don’t Let Logistics Derail You
A destination might look perfect on paper, but how easy is it to get there? Consider travel logistics, especially if you’re bringing your own bike. Many European countries have excellent train connections that allow bikes onboard, while others might require some creative problem-solving (and a good bike box).

Destinations like Girona or Andalucia are well-connected by airports and train networks, making them a breeze for travellers. Remote alpine villages in Switzerland? Spectacular, but be prepared for a few extra steps to get there — worth it for the views, but plan accordingly.

A Few Suggestions to Get You Started:

  • Andalucia: Sunny, scenic and full of rolling hills that make every climb worth the effort.
  • Tuscany: Perfect for those who love a challenge, with rolling landscapes and roads steeped in history (and wine).
  • Switzerland: Breathtaking views, smooth roads and climbs that will leave you in awe (and possibly out of breath).

Pro Tip:
When choosing a destination, think about your fitness level, what kind of scenery inspires you and how much effort you want to put into logistics. And remember: cycling holidays are meant to be fun, not a sufferfest. Choose wisely and your legs — and your sense of adventure — will thank you.

Curving road by a serene turquoise lake in Switzerland, surrounded by lush green hills and dense forested areas with autumn foliage.

Prepping Your Bike and Gear

A well-prepped bike and the right gear can turn a good cycling holiday into a great one. And trust me, you don’t want to realise mid-climb that your saddle feels like a medieval torture device or that your bike’s making sounds better suited to a haunted house. Here’s how to make sure you’re ready to roll.

Gear for Cycling Trips: Pack Smart, Ride Happy

First things first, let’s talk essentials. Your helmet isn’t optional — it’s your best friend in keeping your noggin safe. Pair that with a multi-tool, spare tubes, tyre levers and a pump or CO2 inflator and you’re set to tackle minor mechanical mishaps. Don’t forget lights (even if you’re not planning to ride at night—it’s better to be safe than sorry) and cycling shoes that fit snugly but comfortably.

Now, let’s move on to the comfort department. Padded shorts are an absolute must — seriously, your backside will thank you after a few hours in the saddle. A well-cushioned saddle can make all the difference too, so if yours feels more like a rock than a seat, consider upgrading. Add gloves to prevent blisters and reduce hand fatigue and you’re good to go.

Bike Prep: Show Your Two-Wheeled Steed Some Love

Before you even think about loading your bike onto a plane, train, or roof rack, give it some TLC. If it’s been a while since its last check-up, take it to your local bike shop for a proper service. Get the chain cleaned and lubed, ensure the gears shift smoothly and check the brakes — because stopping isn’t optional.

Choosing the right bike is just as important. For smooth, paved routes, a road bike is your best bet. If your holiday includes a mix of tarmac and gravel paths, a gravel bike or hybrid will handle the job nicely. Whatever you ride, make sure it’s suited to the terrain and distances you’ll be covering.

Pro Tip:
If your bike is making more noises than a grumpy toddler, it’s time for a tune-up before you hit the road.

Prepping your bike and gear might not be the most glamorous part of planning your cycling holiday, but it’s absolutely vital. After all, you can’t enjoy those sweeping mountain views or riverside cafés if your bike’s stuck on the roadside or you’re nursing a blister from dodgy shoes. Treat your gear right and it’ll repay you in spades.


Planning Your Daily Routes

Routes can make or break a cycling holiday. Pick the right ones and you’ll be gliding through scenic wonders with a grin plastered across your face. Pick the wrong ones, and, well… you might find yourself face-to-face with an unexpected 20% gradient, questioning all your life choices. Planning is key and fortunately, it’s not rocket science. Here’s how to do it right.

How to Choose Routes: Finding the Sweet Spot

Start by using mapping tools like Komoot or Strava, which are lifesavers for planning rides that match your fitness level. These apps let you explore routes others have ridden, check out elevation profiles and even preview surfaces — because let’s face it, no one wants to swap smooth tarmac for an unintentional gravel adventure.

A great cycling holiday strikes a balance: some challenging climbs to keep things interesting, but also stretches where you can simply enjoy the scenery (and maybe catch your breath). For example, a classic route might start with a gradual climb, plateau into rolling hills and finish with a scenic descent into a quaint town. Variety keeps the rides engaging and your legs happy.

Tips for Beginners: Keep It Manageable

If it’s your first cycling holiday, ease into it. Start small by planning shorter rides for the first couple of days—think 30–50 km routes rather than century rides. This gives you time to acclimatise, soak in the surroundings and still have enough energy for those all-important post-ride celebrations.

Make rest stops part of the plan, too. Whether it’s a café overlooking a stunning vista or a quiet park bench by a river, these breaks aren’t just about recharging your legs — they’re moments to savour the journey.

And speaking of cafés, don’t forget to include a coffee shop or two in your route. Cyclists run on caffeine—it’s practically a rule. Your legs will thank you and so will your mood.

Pro Tip:
Plot a coffee shop or two into your route. Cyclists run on caffeine — your legs will thank you. And if you find a bakery with good pastries? Congratulations, you’ve just unlocked holiday nirvana.

Planning your routes isn’t just about distance and elevation — it’s about creating an experience. Think scenic points, cultural landmarks and places where you can connect with fellow riders. After all, a great cycling holiday isn’t measured in kilometres; it’s measured in memories.

Close-up of a latte art design in a black cup placed on a rustic wooden table with jars of sugar and cinnamon in the background.

Packing the Essentials (and Luxuries)

Packing for a cycling holiday can feel a bit like preparing for a first date — you don’t want to overdo it, but you also don’t want to find yourself unprepared at a critical moment. Striking the right balance between essentials and a few indulgent extras will keep your rides smooth and your off-bike moments enjoyable.

What to Pack: The Bare Necessities

Let’s start with the essentials, because there’s nothing glamorous about being stranded miles from civilisation without a spare tube or a way to fix it. At the very least, you’ll need:

  • A toolkit: Include a multi-tool, tyre levers, spare tubes and a pump or CO2 inflator.
  • Rain jacket: Because the weather has a wicked sense of humour and it’s best to be prepared.
  • Cycling nutrition: Energy bars, gels, or even a cheeky banana—whatever keeps you going when your legs start questioning your decisions.
  • Water bottle: Staying hydrated is non-negotiable. Pro tip: make it two bottles if you’re tackling longer routes in warm weather.

This basic kit ensures you’re ready for most minor hiccups, whether it’s a flat tyre or an unexpected drizzle.

The Luxuries: Because You Deserve It

Now for the fun stuff — the little extras that enhance a good trip to a great one. Enter the portable espresso maker, proof that humanity truly has its priorities in order. Imagine brewing a fresh shot of coffee while your mates look on with a mix of envy and awe.

Other luxuries worth considering include a travel-size massage roller to soothe tired muscles after a long day and a lightweight camp chair for basking in the evening glow while you recount the day’s adventures. Sure, they’re not essentials, but they do add a touch of indulgence that makes the effort feel worthwhile.

Pro Tip:
Bring layers. No one wants to be the person shivering at the summit or sweating buckets halfway down. Cycling is about finding the perfect balance — both on the bike and in your wardrobe.

Packing isn’t just about functionality — it’s about enhancing the experience. Essentials keep you rolling, but the luxuries? They remind you it’s a holiday, not a boot camp. So, pack smart, throw in a few creature comforts and get ready to pedal in style.


Do’s and Don’ts for First-Time Cycling Holidays

Even the best-laid plans can hit a snag or two, but a little foresight goes a long way. Whether you’re a planning perfectionist or more of a “wing it and hope for the best” type, these do’s and don’ts will help keep your holiday on track.

Do’s: The Golden Rules of Cycling Bliss

  • Do test your gear before you go: There’s nothing worse than discovering your brand-new saddle is about as comfortable as sitting on a brick—midway through a 100-km ride.
  • Do pack light but smart: You don’t need to bring your entire wardrobe, but a couple of layers for changing weather? Absolutely.
  • Do plan your recovery time: Cycling holidays are exhilarating, but they’re also exhausting. Build in some downtime to rest your legs and take in the scenery.

Don’ts: Avoid These Pitfalls Like a Pothole

  • Don’t overestimate your fitness level: That ambitious 120-km route might look tempting, but start with something manageable—your legs will thank you.
  • Don’t skimp on sunscreen: Unless, of course, you fancy looking like a tomato by day three.
  • Don’t forget to enjoy the moment: It’s easy to get caught up in distances and speeds, but remember why you’re there—to have fun and explore.

Pro Tip:
Do pack an extra tube. And don’t forget your pump. Trust me, no one wants to be that cyclist who’s stranded at kilometre 40, waving frantically at passing riders like a shipwrecked sailor.

Cyclist riding along a coastal road during a serene sunset, with ocean views and rugged cliffs in the background.

Your First Cycling Holiday Awaits

And there you have it—everything you need to plan your first cycling holiday like a pro (or at least not like a total rookie). From choosing the right destination to packing smart and embracing the full experience, a little preparation can turn a good trip into a truly unforgettable one.

Cycling holidays aren’t just about the miles you ride; they’re about the memories you make along the way. So, whether you’re tackling rolling hills in Tuscany or soaking up the sunshine in Andalucia, remember to enjoy every moment  —both on and off the bike.

Feeling inspired? Want to skip the hassle of planning and focus on the fun? Explore our guided tours for a stress-free adventure or create your own tailor-made cycling holiday with our private tours. The road is waiting!