Philosophy Of Travel Planning & Logistics

Planning A Really Long Bike Trip? Ask Yourself These 7 Critical Questions First

I know the title of this post might sound odd. For the last 14 (wow… 14!) years, I’ve been banging on about the sheer awesomeness of going on bicycle adventures.

I’ve been doing it so consistently that I’ve now published more words on this blog than in all six Lord Of The Rings books combined.

Why, then, would I want you to question your dream long-distance bike trip?

I’ve been around long enough to have seen a great many bicycle journey-based projects come and go. And – though you’d be forgiven for not noticing – they don’t always end well.

One highfalutin example from a few years back comes to mind, in which a branded, sponsored and massively hyped-up ride from Cornwall to Cape Town barely cleared Western Europe.

The fallout wasn’t pretty. The ‘official’ reasoning from a hostel in Morocco had something to do with travel insurance and security concerns in Mauritania. This was a reasonable-sounding excuse – unless you know that it’s a well-known risk every other cyclist heading for West Africa goes ahead and takes; so far with no reported ill effects whatsoever. Cue epic tantrums when this was pointed out.

It was all rather cringeworthy. Scanning back through the trip blog and reading between the lines, you could tell that this young and inexperienced rider had just been having a really shit time. But buried neck-deep in corporate logos and grand-sounding mission statements, the act of quitting was no longer just a personal decision. It was a public loss of face, the scale of which matched that of the ride’s high-profile departure a few weeks earlier. And that made the whole thing so much worse.

At the private and anecdotal end of the spectrum, I made friends a few years back with a German cycle tourist in Armenia – or, more accurately, former cycle tourist.

After cycling from Germany to Armenia, he’d stopped in Yerevan and had been having far more fun Couchsurfing and hitch-hiking around the Caucasus than he’d ever had on the bike, realising that the whole thing had been lonely and repetitive and was never going to improve.

He’d ended up becoming a more or less permanent resident of Yerevan, in fact, lodging with a long-time Couchsurfer and paying his rent in food (he was a professional chef back home, and a bloody good one at that). The only further cycling he planned to do was to Tabriz, in order to deliver his top-end Rohloff-equipped expedition bike to its Iranian buyer.

These are just two examples that come to mind. I’ve heard countless more, mostly of the private and anecdotal variety.

(No judgement implied, by the way. Sometimes quitting is exactly the right thing to do. I’ve been there.)

It just seems to me that a great deal of energy could be better spent elsewhere if the cycle touring community stopped pretending that long bicycle journeys are for everyone, when the evidence shows that they are not.

So how, dear reader – if you’re planning or considering your first big bike trip – will you know if long distance cycle touring is really for you?

There’s no way to really know, of course, except by giving it a try, which kind of undermines my argument. But here are seven questions to ask yourself that might suggest a likely answer.

(Warning: This is the start of a truly epic 5,673-word blog post, for which you may like to put the kettle on.)

1. Do I enjoy my own company?

Put another way, where do you sit on the introvert-extrovert spectrum?

If you can’t answer that question, it’s possible that you haven’t spent enough time getting to know yourself to know the answer. That might be because you’re too young, or too busy, or just never thought about it before.

Let me tell you: if you’re planning a long cycling journey, you’re about to get to know yourself really, really well.

Even if you’re riding with other people, travelling by bicycle is going to involve long stretches of time when there really is nothing to do but pedal, watch the world go by, and deal with the looming spectre of being by yourself.

One of the less-publicised truths of cycle touring, in fact, is that it generally consists of very little else.

You won’t get this impression from reading blogs or books about long bicycle journeys. The author will be far more likely to spend a couple of thousand words describing the incident with the friendly Kazakh nomad family and the goats’ testicle stew (followed, probably, by “and then I cycled another 500 miles on an empty stomach”).

The act of cycling itself doesn’t get proportional representation in cycle touring stories.


Because it’s boring.

It’s important to know this, particularly if you are planning on going solo; that you will be spending inordinate amounts of time in your own head, with very little in the way of external stimulation to distract you – and no, pedalling is not a distraction any more than breathing is, because by the end of the first week or so, it’s as automatic as it’s ever going to be.

Sure, there’ll be occasions when you’re riding through a scene from a postcard and you stop to gaze in awe. But don’t expect every day to pass like you’re riding through a National Geographic slideshow. Cycling is slow. Changes are gradual. You will see everything, including when there’s nothing to see, and pedalling harder won’t change that.

(I know at least one round-the-world rider who got so bored with the daily grind that he took to watching old episodes of Blackadder on his iPhone.)

Modern Western culture does not have a tradition of proactive training in self-reflection techniques, with the result that we aren’t well-equipped to deal with a prolonged absence of external stimulus. We’re good at dealing with quick-fire material and intellectual issues because we’re confronted by them every day, but when it comes to dealing with the voices in our head, our usual remedy is distraction. Work, play, entertainment, socialising; all can be (and often are) used as avoidance techniques, which of course is why Facebook is so popular because it combines them all.

On a bike, on your own, no common language and a thousand miles of desert to go? There’s nowhere to hide.

The experience of suddenly having little-to-no input can be deeply unnerving. It could be likened to a silent meditation retreat with the instructional element removed.

Anticipate this. I’m not joking when I suggest training yourself in basic meditation techniques (this book* is a good primer) so you will have the tools to recognise and deal with the chattering mental demons that will be unleashed.

But if you have no interest in spending time with yourself (perhaps because you’re afraid of what you might have to confront?) – do yourself a favour and avoid long-distance cycle touring at all costs.

2. Can I tolerate discomfort?

Many of us like the idea of being that rugged outdoorsperson who would sleep through a rainstorm in a ditch with a knife between our teeth and only a handkerchief for shelter.

I do not know anyone who fits this description. And I routinely hang out with rugged outdoorspeople.

We all have limits on the level of discomfort we can tolerate before we burst screaming from our comfort zones and land plonk! in the middle of the panic zone. When there’s no escape from such circumstances, it’s a sure recipe for being really, really miserable.

There’s a certain baseline of discomfort involved in long-distance cycle touring, and it boils down to the fact that while, yes, people’s budgets vary, almost nobody can afford to stay in decent hotels every night for months on end, making wild camping an inevitability. No matter how much you spend on gear, wild camping will mean stressful nights, lumpy ground, soggy sleeping bags, freezing mornings, cramped vestibules and smelly camping partners becoming part and parcel of your existence.

OK with that? Good.

Also, don’t forget that you will be riding a bicycle and spending 99% of your time nowhere near a solid shelter of any kind. You won’t always be able to escape the rain, or snow, or sun, or steep hills, or dogs, or headwinds, or sidewinds, or – my personal favourite – that combination of headwind, sidewind, steep hill, rain, and dog.

If you try to escape all of these things, you will probably find that your cycle tour seems to involve a heck of a lot of trying to work out how long you can reasonably stand under the hot air vents in the doorway of a supermarket before the security guard kicks you out.

Oh – and you will get a sore backside. Guaranteed.

Also; thighs, calves, wrists, neck, shoulders. Pain.

OK, let’s do this properly. I’ll also throw in those concentric white rings of dried sweat on every item of clothing you own; a layer of dark grey or brown grime embroidering every patch of exposed skin on your body; black bicycle grease in the cracks of skin around your fingernails that you suspect may have become tattoo-like in its permanence; the daily frustration of never being able to remember which pannier you put that thing in despite months of refining your packing regime; constantly having to stop and check your direction because you’ve been aiming for the most scenic route possible and all the signs are pointing to the highway; ending your days accosted by locals who just can’t understand that you’re utterly knackered and want nothing more than to sleep in a ditch with a knife between your teeth and only a handkerchief for shelter…

If you enjoy comfort and luxury, and the prospect of that is what makes the day-job tolerable, that is absolutely fine, and you have my permission to book a vehicle-supported cycle tour along the Danube Cycleway with low daily mileages and scheduled lunch stops and a four-star Gasthof every night. No shame. Save yourself the misery of a long bicycle journey and enjoy a hard-earned holiday instead.

3. Can I solve my own problems?

What will you do with you get a flat tyre and your last remaining tube patch won’t stick?

What will you do when your expensive multifuel stove is spluttering black soot everywhere and it’s raining and you’re wondering how long dried pasta needs soaking in cold water before it’s edible?

What will you do when you’re still climbing an endless switchback at sunset and there’s not a square inch of level ground to pitch a tent on?

What will you do when your frame snaps at the rear dropout a week’s ride from the nearest city, it’s 56°C, and you don’t know the Arabic for ‘welder’?

What will you do when there’s no water in the river you’d seen on the map, your bottles are all empty, and it’s four days since you last saw another human being?

What will you do when you discover that your tent pegs don’t work in snow, especially in gale-force wind at ‑33°C in the middle of rural Norway?

What will you do when you’re riding up a mountainous dirt road at walking pace, there’s a crowd of wild Ethiopian children a hundred yards ahead, and the first child stoops for a stone?

Put yourself in each of these situations and ask yourself what you’d do.

You’ll probably find that one of two things happen. Either you’ll start coming up with large numbers of random and untested lateral solutions, or you’ll go completely blank.

Know this: on a long bicycle journey, you’ll be dealing with hundreds of situations like these, and “OK Google” won’t solve any of them. Nor will your insurance company.

Things will happen to test you, and you won’t know what to do; yet it will be entirely upon your shoulders to fix the situation and continue with your ride.

If you’re OK with this – great. Indeed, developing the attitude and initiative to navigate such situations is one of such a journey’s great rewards.

If you’re not OK with it? Well, it shouldn’t stop you setting off, as you’ll learn pretty quick. But it’s good to have an idea of what you’re in for.

4. Do I like to know what’s going to happen?

One of the appeals of the package holiday – which I am not knocking in the slightest – is the near-complete removal of unpredictability. It’s like going into McDonalds for a meal: you know exactly what you’re going to get. Any deviation deeply violates our sense of what is right.

When planning a cycle tour, it is sometimes tempting to try to carry elements of this mentality over, just so there’s something to give us a frame of reference.

If I start from here, at an average of this many miles a day, and I take this route… then I should arrive there on that date.

And yes, there will be certain riders who take this approach and successfully multiply it out, stage by stage, for trips of months or years.

But it is a mistake to assume that this is how things are likely to play out.

Here’s what will actually happen.

You’ll start by getting on your bike and riding purposefully out of town. You do fewer miles on the first day, though, because… well, it’s the first day, and it’s best to ease into it slowly, right?

The following day you’ll mean to set off at sunrise to make up for it, but it turns out there’s a charming little town just down the road to explore (and have breakfast in).

On the way out of town, you’ll realise that it’s a long way to the next supermarket, so you’ll go back into town to stock up for lunch. By midday, you’ll have found a lovely spot by the river that no-one seems to have noticed – with trees for shade – and it’s getting hot, anyway, so a little lie down after lunch makes sense.

While you’re napping, a farmer will spot you and invite you over for a second lunch (why, thank you!), and tell you there’s a much nicer route in the direction you’re going, if a little longer and more hilly. Then it’ll turn out that he’s more interested in wine than food, and now you’re over the limit too. In any case, his wife will have offered to let you camp out back.

In the space of a day, you’ll realise that not only could you easily spend twice as long as you planned getting from A to B, but you’d probably have a lot more fun if you did. You might even have realised that heading towards C makes more sense than B.

How does this style of travel sit with you?

Just asking. Because sticking stubbornly to your sensible, pre-planned itinerary will inevitably mean saying no to the charming town, no to the shady lunch spot, no to the farmer’s kind invitation, no to the scenic route.

And, over time, all those nos can add up to a lot of resentment and frustration.

If you’re able to build the kind of flexibility into your plans that will allow you to act spontaneously to new opportunities, you’ll be embracing what for me is the real spirit of the bicycle adventure: the freedom afforded by this humble mode of transport to go anywhere, take every opportunity, and do it all entirely under your own steam.

If you need things to go exactly the way you’ve planned all the time to feel that you’re in control of your life, on the other hand, the idiosyncrasies of the long bicycle journey may simply stress you out.

And if that stress brings you to breaking point, you have two options – either quit stressing and go with the flow, or quit riding and go home.

(One more reason not to make any public promises you can’t keep.)

5. Am I capable of living in the present?

Modern life tends to be overwhelmingly oriented towards goals, targets, objectives and deadlines – especially in the context of work, which of course constitutes our main hobby in the developed world.

When we take a break from work, it’s natural to want to drop out of this mindset and to enjoy the present moment. But – though it sometimes feels like it could go on forever – it’s rarely long before we return to our previous goal-oriented state.

Something funny can happen when we take a much longer chunk of time out, however, or when we quit our jobs altogether in order to travel. We are creatures of habit, and it doesn’t take long before we start to crave a new goal to work towards, because that’s how we’ve come to understand purpose and progress in life. And so we begin to invent goals and objectives to work towards.

(Perhaps this explains the incidence of high-powered professionals reinventing themselves as adventurer-conquerors on a mission to push the limits of endurance and human capability.)

The elephant in the room in the context of bicycle travel stems from the combination of goals taking the form of far-off destinations (let’s take cycling from the UK to Australia as an example) and the bicycle being absolutely the slowest and most inconvenient way to get to that destination.

If you simply want to get from the UK to Australia, there are a number of perfectly decent airlines who will accomplish this for you in roughly 24 hours, as opposed to the year or two it would take on a bicycle, and for a lot less money.

Choosing to make that journey – or any other really long journey – by bicycle, then, must mean that arriving at the destination is not the point at all.

I remember chatting to one fresh-faced youngster at RGS Explore many years ago, shortly after returning from my first long bicycle journey, where I’d been asked to sit on the panel for the cycling expeditions workshop.

“But what were you actually thinking about when you were riding?”, he asked me earnestly.

“Erm…” I began, and paused, slightly taken aback, because it had never occurred to me that there was a simple answer to the question of what someone had spent the previous 3½ years thinking about.

But the young man misinterpreted my hesitation as an implication that the answer should have been obvious, and, nodding gravely, filled in the answer for me.

“Just focusing on the mission.”


Of all the millions of things I no doubt thought about while pedalling all those thousands of miles, the one thing I can safely say I never, ever thought about was…

The mission.

I thought about lots of things. I thought about everything. I thought until my brain was so exhausted from thinking that everything went very, very quiet, and I realised I had nothing left to think about, except for the most immediate concerns of the moment, if indeed there were any. And if there weren’t? Well, I contented myself with entering that most rare and unimaginable of mental states: not thinking about anything at all.

Oh, if only I could have explained that!

It boils down to this: if you spend your days holding some intercontinental finish line in your mind while you’re grinding along at 13mph (and you’re not consciously doing this thing in order to break a world record, make a TV show and launch a career off the back of it), you will go completely barmy.

That finish line will never get any closer. You’re on a fricken’ bicycle. You may be looking at a journey of months; even years. Why would you choose the most fiercely independent form of global travel and then fritter away that freedom waiting for your journey to end, one futile pedal stroke at a time?

You won’t get any special points or awards for suffering in this way. It won’t make you stronger or better as a person. It just means you’ll have missed the point completely.

The use of almost every other mode of transport – cars, trains, buses, planes – can be characterised by enduring the process of arriving at a destination. Carrying this way of thinking over to the bicycle – at that kind of scale – is a mistake.

By all means use a far-off destination (or series thereof) as a bearing for your overall direction. But once that bearing is set, look up from the map and compass and experience the journey itself, for that is where the rewards of bicycle travel truly lie.

Incidentally, there’s a cliché going around at the moment about ‘mindfulness’ and ‘being present’. It seems to be an antidote to that goal-oriented mentality; a tool that allows us to take little breaks from the futility of trying against all odds to wrangle the future into a pre-determined shape.

On a long enough bike trip, you’ll come to terms with the reality that it really is only possible to experience the present, and that the past and the future really are just constructs. You won’t need any bestselling books or guided audio meditations or expensive retreats to discover this, because the truth will be forcefully thrust in your face.

(Hah! And here I am, talking about your future…)

An important postscript to this point.

You may have decided to social media the crap out of your journey for whatever reason. Having begun, you may have realised how complex the experience is that you’re having, and feel the need to dumb things down for ‘your audience’, numbering your days and posting a daily mileage count on Facebook.

If this is you, please consider that you may be taking advantage of the ignorance of an awful lot of good people when it comes to what life on the road is actually like, thus propagating the myth that such a journey can be meaningfully reduced to two-dimensional statistics and a line on a map. It can’t.

This is not to say such stories are not worth sharing, but let’s at least be honest and open about that fact.

6. Am I hoping for social recognition/approval/status?

Spend some time with this one. Because there is always a deeper motive behind an idealistic-sounding desire to drop out of the system and pedal across a couple of continents.

Sometimes it’s a desire to escape a stifling set of life circumstances and strip everything down to the essentials in order to feel alive or unconstrained or authentic. Sometimes it’s a desire to imitate or follow in the footsteps of a hero or idol and live out a fantasy for oneself. Sometimes it’s a reaction to discovering that the world is not as it appears on TV and wanting to supplement that with first-hand experience. Sometimes it’s something private and unimaginable.

(The common theme is often simply that the bicycle is chosen a means to an end. People relatively rarely go on long bike trips for a love of cycling.)

Sometimes, though, what drives a journey like this is a desire to make some sort of statement to society – that a wrong turn has been taken and this journey will illuminate the right way. This one is different because success or failure depends – at least in part – on the perceptions of others.

There may be a personal injustice involved, or an inferiority complex, and the ride is about retribution in the eyes of those who caused that pain, even if only in theory.

Or there may be a greater social issue at stake, and the ride has been cast as a way of raising awareness of it (or, in a minority of cases, actually doing something about it).

This is dangerous territory, for a few reasons. The most obvious of these is that you can’t imagine it unless you’ve been there.

Riding a bicycle round the planet (or a good chunk thereof) is an intensely affecting experience, calling into question ways of thinking and living you don’t even know you take for granted until you’re faced with the evidence. It’s often humiliating in the original sense of the word – it will make you humble, bring you down a peg or twelve.

In that light, any hopes that your exploits will elevate you to a position of respect or superiority will be dashed, because your insecurities will have paled in comparison against the tangible and often mortal struggles of so many in the world. And while you know you could spin your tale in a way that makes everyone back home think you’re awesome, you will always know that your story is a fraud; that all you really did was get on a bicycle and start pedalling, like four-year-olds in backyards all over the world are doing right now, and you transiently experienced a lot of asphalt and a hell of a lot of other people’s versions of normality while you were doing so, and when you put it like that, it’s not so awesome after all.

A less distasteful and entirely understandable desire is simply for your friends and family to understand what your journey was like, and to ask kind and curious questions about it when you come home. Again, you will be disappointed.

Almost nobody will ever understand what you experienced or how it changed you.

The experience you’re going to have lies outside almost every frame of reference we collectively share – how big the world is, how strangers really behave when the evidence is averaged out, what it’s like between places, how it feels to live with no top-down control structures whatsoever, how constantly moving at 13mph affects time and memory, how communication and relationships change when you meet a hundred new people every day, how it feels to spend most of your waking hours having no idea how or where your day will end, how it feels when you put your body into full-time service as an engine for transport…

These, the things that define the lifestyle, are things that not only will your closest people never experience, but they are things that you will find you lack the ability to explain, because for most of it, there is no familiar form of words to put it into.

(My theory is that this is why so many long-haul riders end up writing books and blogs – they simply want to devote sufficient time to articulating the experience.)

Attaching a ‘cause’ – by which I mean a charitable, political, fundraising or similar project – to a journey is also, in my opinion, a dangerous move.

This is not because there’s anything innately wrong with doing so. After all, it’s natural (and accurate) to think that people will be interested in following your story, and that if telling your story well can bring attention to another issue, why not do so?

The problem is twofold. There is first the additional layer of intellectual complexity that it will add to your trip. You’ll need to attend to the cause consciously, strategically, and with consistency, and you’ll need to wrestle your stories to make them relevant, if the effort is to pay off.

You’ll also possibly need to portray the cause as the whole point of the endeavour – at least, if you expect anyone to believe that you haven’t just tacked it on to justify an extended holiday. And that might not be true.

The second problem is that going on a bike trip of months or years is a really ineffective strategy for achieving something tangible in terms of fundraising or awareness-raising. Kickstarter campaigns, flash sales, presidential elections – these things take the form of a short-lived burst of activity for a good reason, which is that people quickly get too bored to take any action.

You, on the other hand, will have festooned your website, Facebook page and Twitter bio with logos and links to your cause. But after the first hit, your audience will either have devoured it all/donated cash/changed the way they live their life; or they will erect a filter which prevents them ever seeing or thinking about your cause ever again because what they are really interested in is the story of your bicycle adventure.

There are exceptions – usually time-limited and high-profile exceptions with massive amounts of forethought paid to the whole operation.

But otherwise you’ll almost certainly better advance your cause by doing a speaking tour after your ride has finished, giving all the proceeds to charity, and moving on.

You’ll find a lot of stuff on the internet to do with big fancy bike trips which look like they’re getting lots of attention or raising awareness or inspiring others or whatever. Just be aware that anyone who is painting such a picture may have an axe to grind that you will not be aware of, and/or may have painted a distorted picture of the reality of their ride and motivations for doing it. In other words, beware of selective storytelling.

Be aware, also, that for each of these examples there will be a hundred others you’ll never hear of unless you happen to meet them on a roadside somewhere, because they don’t have a blog or a social media following and couldn’t care less because they’re doing it for the hell of it.

My advice? Take your cue from that latter bunch unless you’ve got a really, really good reason not to.

7. Can I deal with a major & irreversible change of perspective?

Finally, please do not embark upon a long bicycle journey if you are expecting it to confirm everything you think you know about how the world works. You will be sorely disappointed.

The truth – and this is a common theme I’ve heard repeated ad nauseam from tons of other long-haul riders – is that you will likely have any and all preconceptions dashed against the rocks of reality.

(Except for getting a puncture. This I can guarantee.)

This will happen on multiple levels simultaneously and over an extended period of time. Really, it’ll be less of a rock-dashing and more of a gradual erosion. It may take a similar amount of time for you to process what has happened and make any kind of sense of it. It may even be that you will never make sense of it, or identify anything concrete or tangible about what is really an accumulation of events that momentarily surprise you and cause the most imperceptible of mutations in your context for the events and discoveries of life.

But you will one day realise that you have undergone a major change of perspective.

If this all sounds rather mysterious, read Janapar, which is largely an attempt to try and make sense of what happened during my 3½-year introduction to bicycle travel.

Anyway, my point is not how your perspective will shift – you’ll discover that for yourself. The point is only that it will.

This will have a few effects that you may not expect. You may, for example, behold the fantasy that after your big bike trip you will become one of those rare dinner party guests who always has the most unbeatable anecdotes for any conversation, tales imbued with a perceptive wisdom and gentle humour, delivered endearingly with a notable lack of arrogance. An overbearing fellow diner will get ratty that you’re stealing the limelight, but you’ll deal with this with a masterful sidestep that simultaneously brings the antagonist onside and makes everyone else think you’re even more of a legend. Women will want to be with you, men will want to be you. (Or the vice versa.)

This is not what will happen at all.

Instead, you will be the dinner party guest who sits silently and awkwardly while everyone else discusses commuting times and dog ownership and the many ways in which the house could be extended or renovated or redecorated; the choice between one or another shade of non-drip satin in the latest Farrow & Ball catalogue. Bored shitless, you’ll tear a hunk of bread in half and scour the remains of the boeuf bourguignon out of the bottom of your bowl and stuff it into your face before realising that everyone is casting furtive glances at you during a strange lull in conversation. You’ll look out the window and notice that the washing line is just high enough and that patch of lawn just big enough to squeeze a 2‑berth ultralight tent in there. You’ll get up to leave and realise that you are the only one wearing zip-off trekking trousers with a distinctly Brooks-shaped curve of threadbare fabric upon each buttock.

(If your host was unfortunate enough to have introduced you as ‘the guy/girl who cycled round the world’, by the way, you will at this point be considering lingering until the other guests have left in order to take them out back and ‘teach them a lesson’.)

Your change of perspective will bring with it much in the way of clarity. This is nice. It will also make you feel, regularly and consistently, as though you are living on an entirely different planet from every other human on Earth. You will fall into a pattern of feigned interest combined with self-censorship in order to lubricate those few remaining social situations from which you can’t excuse yourself.

To your relief, you’ll one day discover that you’re part of a tiny and scattered association of other riders who’ve actually got some shared context for what you’ve seen and experienced. You’ll start to crave their occasional company, feel lonely when you don’t have it, and wish there were some kind of real life meet-up – even just occasionally – for people who actually get it. (You might even end up creating one.)

And one day you will realise that you may simply have to make peace with all of this.

If, having had a good think, you’re more or less sure you’re OK with all of that, then by all means embark on a long distance bicycle journey.

I have never met anyone who regrets doing so.

Just don’t say I didn’t warn you.