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 15 (wow… 15!) 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, 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 exhausted 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 a bit of comfort and luxury on an adventure, 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 when you get a flat tyre, your last remaining tube patch won’t stick, your spare innertube is the wrong size, and you’re in the middle of Outer Mongolia?

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 road 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, in gale-force winds at ‑33°C in the middle of rural Norway, that regular tent pegs don’t work in snow?

What will you do when you’re riding a walking pace up a mountainous dirt road, there’s a crowd of children a hundred yards ahead, and the first one 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.

And yes – all the stories above are true.

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 in reality.

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 ride 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 they’re more interested in wine than food, and now you’re over the limit too. In any case, they’ve 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 life and 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 react 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, accept every invitation, take every scenic route, and do it at whatever pace feels right at the time.

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 corporate executives reinventing themselves as professional adventurers 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 one of the slowest and most inconvenient ways 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 broadcasting 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’ll just mean 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, ‘mindfulness’ and ‘being present’ has become ever more trendy since I originally wrote this post. Many of the techniques could be viewed as an antidote to that goal-oriented mentality; a toolkit 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 eventually figure out for yourself 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 app subscriptions to discover this, because the truth will be staring you in the face all along.

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

An important postscript to this point.

You may have decided to social media the fuck 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, posting a daily mileage count, and trendily oversharing how much internal self-doubt you’re dealing with right now.

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, a line on a map, and trite anecdotes about your inner journey. It can’t.

This is not to say such stories are not worth sharing, but let’s at least acknowledge the possibility that they might be better off digested before being regurgitated.

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. Though there are exceptions, people 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 external perceptions.

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 their opposites. It’s often humiliating in the original sense of the word – it will make you humble; bring you down a peg.

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 towards each other, 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 live every day having no idea where you’re going to sleep, how it feels to 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 some time to articulating what it all meant to them.)

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 an ineffective fundraising or awareness-raising strategy. 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 have very short attention spans.

You, on the other hand, will have festooned your website and social media bios 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/etc; or they will have erected a filter which prevents them ever thinking about your cause 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 considerable amounts of professional marketing and communications expertise baked into 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 love, man.

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 life. You will be sorely disappointed.

The truth – and this is a 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.

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 and irreversible change of perspective.

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; tales imbued with a perceptive wisdom and gentle humour, delivered endearingly and 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.

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 vegan 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 one 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 a different planet from every other human on Earth. To survive, you will fall into a pattern of feigned interest combined with regular 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 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.

Bogged down in research for your next big bicycle adventure?

I wrote a whole book to help with that. How To Hit The Road is designed to be read at your leisure, making planning a bike tour simple and achievable, no matter the length, duration or budget. Available globally as an ebook or paperback.

Comments (skip to respond)

72 responses to “Planning A Really Long Bike Trip? Ask Yourself These 7 Critical Questions First”

  1. Mark Hayden avatar
    Mark Hayden

    Sounds good to me. And just in case I’ll say it now. You warned me.

  2. I’ve been that dinner party guest so many times. Coming back is harder than leaving.Keep travelling while you can ??

  3. TJ McDonald avatar
    TJ McDonald

    Thanks for this. I just bailed on a solo US cross country trip in Nebraska. I thought I knew the answers, but found out I couldn’t say yes to one and two. I am not as comfortable with myself as I thought. I had great times with people on the road, but they didn’t satisfy me as I thought they would. On the positive side I got closer to my son because we called everyday. I rarely told him I loved him. Now I do it every phone call. I also discovered that I don’t handle discomfort as well as I thought. I was in the Peace Corps on an atoll and backpack, but being solo in a crappy camping situation was awful for me. It’s hard not to feel disappointed in myself, but it’s helped me realize who I am now.

  4. You are a master of the language Tom. Much has been written in journals and blogs about bicycle travel, and much is frightfully rough. Yours is amusing, concise, and a joy to read.

    Regarding your Seven Critical Questions, I whole heartily agree some serious introspection is wise before one launches a cycling expedition spanning a continent. The points are as valid today as they were eight years ago when you created the post. However, I’d like to suggest there is an important dimension of geography when answering the Critical Questions. It’s one thing to be stranded on the Serengeti and burn wildebeest dung for survival. It’s quite a different thing to be stranded on the American Prairie and nip into Starbucks for survival. 

    My first, and only long distance cycling adventure was the TransAm trail last year ( To your Critical Question #7, “Can I deal with a major & irreversible change of perspective?” I am reminded of a thought-provoking, insightful question I was asked on Day 42: “How has this trip changed you?” I’ve thought long about that question, and my somewhat plausible, somewhat nebulous answer hinges on an understanding, appreciation, and tolerance of the differences in people. I had never really listened before.

    Whatever the perspective shift, it was great enough for me to do it again. East coast U.S.A. this year, where nary a wildebeest will be found.

  5. Thank you very much for writing this. Reading this article was like peeking into an escape hatch from the normality of ordinary life.

    I haven’t been on any cycling tours yet (even for a 1 night) however I’m planning to do some this season. This article was inspiring to me and much more than that. Giving me answers to the questions I did not know I wanted to ask.

    1. Very glad you found this article inspiring, Denis. I wrote it for exactly the reason you mention – if you hadn’t done such a trip, you probably wouldn’t know to ask these questions…

  6. Glad I found this page Tom. I was seriously considering partnering with a nonprofit and really spreading the message of their organization, hoping it would give me incentive to follow through, but I may keep it on the backburner and only bring it up if people ask. The post-ride interview idea is genius!

  7. […] solo long distance overland probably far better and in more detail than I ever could. Tom Allen’s blog about cycle touring is excellent. Nathan Millward’s blog about The Hitchhiker (not online at the moment) and his book […]

  8. Ken Harrington avatar
    Ken Harrington

    This is by far, the most eye opening, spot on, real definition that I’ve ever read. I’ve never been able to put it in words, and you did an excellent job for me. Biking, and/or traveling, completely changes your perspective of life. And there is no going back. You are changed forever. And sometimes it’s very difficult if not impossible to express those changes and feelings to lay people. The hardest thing I’ve ever had to deal with is trying to fit back into “normal” society. You are changed for life. And you’ll never be “normal” again. It’s a concept very few can relate to much less handle.

    1. That’s very high praise, Ken. I appreciate your comment. It took years of riding before I felt ready to write this. And I would still point to it as my single most important piece of advice for anyone considering a long-term bike journey.

  9. Robert Johnson avatar
    Robert Johnson

    So good to see a writer not rising to a troll like comment from Anthony. Well done.
    And, by the way, a well written discourse on long trips.

  10. I remember reading this article before my 3 months long cycle trip. Then, i did not really give much credence to the article. After going on that trip and reading this article now, I can totally understand the main point that you were making. Such an honest article that every dreamy cycle tourer should read first. The problem, like you identified, is that you dont really know until you do it. So, its good to go on a mini trip to make sure you know what you signed up for!

  11. ian partridge avatar
    ian partridge

    Well I enjoyed the read. Sobering. …
    I retire this year at 65, I’m off on a bike with the possibility of not returning, I’m a bit frightened, I like that.
    Ian UK.

  12. Traffic hazard avatar
    Traffic hazard

    I’m getting wanderlust with summer here. But my previous experience with cycle touring did not go well. I attempted to cycle the trans America trail. I felt like I could have handled all the deprivations and enjoyed the experience but for the motor vehicles. After being constantly buzzed by trucks and RVs for days on end, with nerves fraying, I finally had to admit that I was having a terrible time. I quit without ever leaving Oregon. Maybe cycle touring just isn’t for me? Or was I doing it wrong? This experience left me wondering: why is bike touring even a thing? I’d be interested in giving it another try, since there were some great moments too, but I can’t answer the question of why it would be different this time. Any advice or thoughts?

    1. My advice would be to seek out routes that aren’t shared with trucks and RVs! I appreciate that’s not entirely simple to achieve, but it is possible…

  13. Tom,

    Your words hit me like a punch in the belly. In a good way, that is. I’ve never read such an honest account of traveling in a bike. So, thanks for the huge heads-up.… 

    I’m planning on starting bike touring here in Portugal, with some small 2–3 day trips just to try it out first and see how I feel, before going head-on on a 2 week ride. 

    I was a regular Mountain and Road cyclist, attended some events and pedaled for a few thousand kilometers before I started to feel it. The emptiness of just going somewhere, stopping for a few minutes, and coming back. I needed more. To stay, listen, and see better the places that I zipped accross so fast. I think I can relate to what you say above.

    So, thanks a lot. This blog of yours is an inspiration. But one in the real world.


  14. Hi Tom,

    Just discovered this website and I’ve been reading it for two hours now! Fantastic stuff. I love your honesty and your wicked turn of phrase. 

    I am planning a nice little 8k trip myself and was somewhat pleased to discover that my thought processes and questions are somewhat aligned with your own. The first one is interesting as I may start talking to trees and stones and mountains. My bike and I go way back and mostly she ignores me. Two through five I am happy with and excited by. Six not so much; it’ll be private. Seven, guilty a little. Ok a lot but I laughed at myself while reading your blog. 

    I just want to see things and meet people along the way. I’ll be prepared, somewhat but yeah I’ll get a plane, hitch a lift with a truck and then turn around and start heading south until I see ocean. 

    Thanks for inspiring and reaffirming


  15. Jim Osage avatar
    Jim Osage

    These are hard questions to even conceive of, much less explain in such a perceptive and understandable manner. The article is so well written. I’m jealous. Thank you.
    I think I had a question but I can’t remember it.
    Wind at your back, eh.

  16. Hi Tom, thanks for your post. The length seems to indicate that, after all the tours, you’re still trying to figure this stuff out for yourself, which is great. I’m recently back from a 9 month tour and I think, yes, it’s a cliche, but it is about the journey. And being true to yourself. I need constant motion and have cycled since I was little. I wanted to want to settle down, but there’s a deep desire to get back on my bike and keep learning. Is that ok? Is it any way to live? I think from reading your post that it is. So thanks for the encouragement (again). Cheers.

  17. Well I like cycling but after asking myself your 7 questions, I know that I’m not ready for a long-distance journey. But maybe I will follow your guide as well as your post, and someday I will be ready. Thank you for an inspiring post, Tom. Wish you all the best on your journeys.

  18. Fantastic and honest article .

    I know my own limitations and for me at this point in life the 5 or 6 day local tour is just enough .
    Even at that I have learned to see each of these short tours as a tough challenge that will benefit my character and enrich me in ways most of the routines in life don’t . This mindset opens me up and puts me in a much better mental place for bike trips than when I expected to have a rosy fun filled holiday on my bike . The challenge of spending time alone is a point well explored . You can learn a lot about yourself spending days cycling and see things in yourself you might not want to see . There is a therapeutic element too . Even after short trips I often feel like I have untangled something within me just from spending time with and breathing deeply into thoughts and emotions that bubble up .

  19. Hi Tom ,
    I got a lot of inspiration from the article
    It strengthened and sharpened my thoughts
    Touring bike journey is a journy of one into himself

  20. John Ford avatar
    John Ford

    Thoughtful and well written .. thank you Tom.

    Bicycle touring is reality on wheels. We are socialised to crave distraction .. to switch continually from this to that .. to seek ‘stuff’ with the idea that in accumulating ‘stuff’ will somehow alleviate the loneliness we feel deep inside. All this is a facade while our true ‘self’ lies buried under the garbage. Long distance touring is like have a long hot shower after a dusty 100 kilometre stage .. it cleans off the facade and we see the world as it really is .. then we realise what it means to be free .. to ‘get’ it.

  21. Simon avatar

    Great article Tom

  22. Tony Patchett avatar
    Tony Patchett

    What can I say, you may as well have jumped inside my brain to confirm EVERYTHING that I’ve been thinking of their the past 6 years. Thank you so much for such a perfectly written article. I have set myself 2 years to back myself out of life’s commitments and then I am gone. I can’t wait and this article has made me nothing if even more excited and impatient to jump on my bike and just keep going. Thank you!

  23. Randy avatar

    So knowing that I am planning on Philadelphia PA to Key West FL and back in 2018. I gave my wife (the only person who actually knows me and understands the logic) this article to read. She gave it back to me and said,well you are 7 out of 7 you are definitely going then. Not that there was any doubt. Thank you for a great article, and reassurance as to why I am going and that very few people under stand..

  24. Lord Of The Flies Guided Reading Questions |

    […] Planning Your First Big Bike Trip? … – There’s no way to know for sure if cycle touring is for you, except by trying it. But asking yourself these seven questions might suggest a likely answer… […]

  25. Scott Burrowes avatar
    Scott Burrowes

    I’m blown away by how you can articulate your (and my) weaknesses in a way that seems so ruthless and yet leaves me chuckling and forgiving of myself. The hope vs. reality of what sort of dinner party guest you’ll be… So on the money!

    I’ve been off the road a while, itching to get back on but adamant I won’t set off again for the wrong reasons. My passion has been checked by a hesitance I’ve struggled to define, yet here I think you’ve laid most of it out for me. Whether I’ll go this year or not, I’m still not certain, but I feel much closer to a decision either way because you’ve helped boil it down (into merely thousands of words) in that special way that you do.

    Much gratitude from a regular reader.

    1. Thanks Scott 😀

  26. Hey Tom, do you think you can actually get back to (be comfortable in) the ordinary world that you described at the dinner table? Does it get easier after you have lived with the change in perspective for a few years? This is something that I struggle with every time I come home after a very long trip. After a few long periods abroad I have become more comfortable with the disconnection but it still leads me to believe finding common dialog will be forever be rare.

    1. I’m not sure it’s got easier, but I’ve definitely learned to accept it. There will always be old friends with whom I share happy memories of ‘before’, and there’ll always be new friends who I’ve made because there’s a common dialog to be had. The rest of the time, I content myself with the feeling that I’m living on an entirely different planet 🙂

  27. I’ve read quite a few of your articles now Tom and I think this one is the best you’ve ever written. I feel the passion in each line. Loving the love-hate relationships in each simple touring task. Nice one.

  28. Doug Peterson avatar
    Doug Peterson

    Well done, Tom. Such a thoughtful & thorough consideration of many issues. I must admit that after reading the title & intro, my first thought was that should one need to work through these questions, perhaps such an adventure was not for them. All considered, you’ve outlined it quite nicely. Leaving the change aspect to the end was a nice touch. Many embark on epic journeys in search of themselves, and can be surprised at what they find. As to point 3, I’ve suggested that as long as one wakes up in a different place tomorrow, you have traveled, be it 30 miles or 100 miles. Granted, on your journeys many regions look the same for hundreds of miles, but movement has occurred. Thanks for the thoughts.

    Doug Peterson

  29. I really enjoyed reading this, great share 🙂

  30. Campbell avatar

    Hi Tom,
    Great article — some interesting food for thought as I’m heading off in a couple of months on my first big tour (Peru to Patagonia)! You mentioned a book about basic meditation techniques but, I think, ommitted the link — what was it?

      1. Campbell avatar

        Great, thanks very much.

  31. When I was 16 I wrote a “letter to myself 25 years from now” as an assignment. Mine started out with “Did you ever bike across the country?” or something to that effect. I am now approaching 59 and hope to realize my dream before I am 65. Long distance cycling is something which has always appealed to me and something I have striven toward. At this point, I have my bike (Surly), gear (everything but the stove at this point), and have started taking 3–5 day trips which I have thoroughly enjoyed. While I had not considered all the questions raised by your article, I had some and your insight was much appreciated, in part, because your answers supported much of my own thoughts on the matter. Thanks for articulating the questions and responses so well. From one “travelin’ tom” to another! Thanks again

  32. […] about the realities of cycle touring much better than we have been able to articulate, check out this blog. We felt strangely emotional about our whole experience after reading […]

  33. Nigel P avatar

    Thank you Tom for a very illuminating and thought provoking article. Much appreciated.

  34. Mark E. Martin avatar
    Mark E. Martin

    Let me add my thanks to that of others, Tom. I am fortunate to host bicycle tourists when they pass through Baton Rouge. It is a great pleasure to speak to like minded people and receive their encouragement to go on that long trip I’ve been planning. Your words add to that encouragement. Thank you!

  35. Allen Ashworth avatar
    Allen Ashworth

    Great article Tom. Well written with the benefit of experience. I believe that a cycle tour is like a story book, it needs a beginning a middle and an end. You can get a good idea of what it will be like by reading the reviews. But the only way to really know what it will be like is to open the cover. Newbies will read articles, blogs, books and watch endless utube vids and believe they know what it will be like. They would be wrong. The only way, as you so rightly say, is to put your bum on a saddle and push the peddles.
    Looking forward to seeing you at the Cycle Touring Festival

  36. Tom — Great article. Having completed the TransAm last year I had no idea if I was suited for biking touring or why the disire. I’ve had the itch to try bike touring since a teenager (now 58) but never pulled the trigger. I have always enjoyed bike riding, and continue to today. Turns out I’m well suited for bike touring. I wish I had your 7 questions before I started, it would eliminated lots of doubt prior to the start.
    I may be somewhat unique but the joy of being on a bike all day is all I could ask for. Yes, the people I met and the beautiful sites were a treat as well.
    My mantra for the trip was, “how bad could it be, you’re riding your bike all day.” Yes, and some nights as well.
    My observation when it comes to bike riding is if you have what I call the “bike bug.” This is joy being on a bicycle. It can hit you at any age and its with you for life. I really enjoy seeing this happen to someone older.
    Thanks again for the thought provoking read Tom

  37. Excellent article Tom. I think the point about being comfortable with discomfort is an important one. When I’m trying to explain what cycle-touring is like to people I meet on the road I often say “it’s only as hard as you choose to make it for yourself”. This is only mostly true though. It’s a good thing to say because it gets over the point that you don’t have to be in any way special or extra-ordinary to do a long bike trip. I consider myself living proof of that. However, the truth is that you will from time to time, either deliberately or unwittingly, put yourself in demanding and uncomfortable situations: The weather can turn visciously against you, you take a wrong turn into particularly difficult terrain, or you simply come to realise that often the most scenic, awe-inspiring terrain is in the mountains, where riding is inherently more challenging, sometimes pushing you well beyond your comfort zone. It’s also true that while these situations can be excruciating at the time, in retrospect they often form the basis of one’s most treasured memories and certainly the most entertaining stories.

  38. mattman avatar

    Great article Tom.
    I’m tentitively planning my big trip next year. I have been cycle touring for years and I am going out for 6 weeks this summer as partial preparation.

    The plan is every country in Europe on one trip.

    There is much wisdom in what you say above. I love the bit about eventually being forced to live in the now. So true.

    Two points from me:
    Cycle touring on your own, you are effectively a tramp, a hobo. You have very little. You own nothing really but a bike and a tent. If you lose your spoon that is important — you are eating with a fork. (Hint — don’t lose the fork). Life is stripped to basics.

    You meet people on your own and people are, generally, kind and lovely. You need good manners but folk often take pity on you and feed you/provide you with water/help/company. Talking to people is always a joy and finding out about them and their lives is usually fascinating. All you have to do is ask, be interested and listen. 

    I’m looking forward to reading the rest of your stuff — you write well.

    All the best,


  39. Just fantastic, Tom. Thanks for this long-post-short-journey over the real facts.
    Your brilliant (and brave) point of view seems to apply not only to long-rides, but to a small thing that many call “life”.

    I didn’t know you before the ride. Well, OK, I didn’t know today, I’ve just watched/read the small imperfects fragments of your perception of your big journey. Great book and film, by the way. But I’m pretty sure that all the hell (and heaven) you’ve been make you a incredible person. This text is a proof.

    Thank you, Tom!

  40. “People relatively rarely go on long bike trips for a love of cycling”

    …Oh, but you get to ride a bike everyday and riding a bike is amazing! 😉

    1. That’s the added bonus 🙂

  41. Hey Tom,
    thank you for sharing this article. (I expected the typical ten point program, so I was a bit disappointed it ended with 7., I was wanting more):-)

    I loved the article, because I always like to think that everyone can go bicycle touring if they want and I still think this is kind of true.…you just have to consider a couple of things. 

    Also, I totally agree to your points made, I feel like it might discourage people in pursuing their dream. There is not really anything which can prepare you for bicycle travel.…not even a gear-testing weekend trip or a couple of nights out camping in the woods. So the only way to find out, is hitting the road. If you surrender fine, you are probably able to sell all your high-end gear and make back some of that money you spent, possibly your family will be relieved about your early return and your friends will forget about your misadventure over their second pint. No biggie. The other side though, not starting your trip, because you are scared and don’t think you can handle it…will doubtless end up in life-long regrets. So why discourage and warn people? It’s not like they are going to die, if it does not work out.

    When we first started traveling by bicycle, we bought two cheap bikes, made our own panniers and did not even google “bicycle touring” once. I’m glad we started totally dewy-eyed.

    1. Absolutely agree – this is why I began the article by saying that “there’s no way to really know, of course, except by giving it a try”, and ended it by saying “I have never met anyone who regrets doing so” 😉

      1. Nice article tom. I will bookmark your blog today. So much to read and learn.

  42. Geoff Tervet avatar
    Geoff Tervet

    Excellent article! Thank you.

  43. Libby Ranzetta avatar
    Libby Ranzetta

    Really enjoyed thinking about this lot Tom, especially number 7, which made me realise that, as a scaredy-cat pessimistic wimp, that the main objective of my forthcoming adventures is to have a ‘major & irreversible change of perspective.’

    1. I don’t doubt you’ll get it! Where are you heading?

      1. Libby Ranzetta avatar
        Libby Ranzetta

        Suffolk to Brighton and back as a test run, and then the North Sea Cycle Route (if I can work out how to get from Bergen to Scotland with dog and trailer.)

  44. This is exceptionally well written. There’s only one of these i feel particularly iffy about which is the can I solve my own problems. Which is partly the reason why my first cycle tour is cycling America in about 5 weeks time. (Oh gosh!) As I’m sure that I won’t have too much trouble in finding people who can solve my problems for me, should I happen to struggle somewhere along the way. Couldn’t explain the point A‑B thing better. I recently had this discussion at work and glad that I’m naturally on the right lines. Cheers Tom, great read.

    1. Yes – it is often a case of taking the initiative to find someone else to help solve your problems on the road. Some find this just as difficult!

      1. Anne Mustoe wrote that she set off on her first tour not knowing how to mend a puncture, and never did learn how to. She always found someone who could.

        1. Cardeal avatar

          I have a friend who uses me as her google. I told her I would teach her how to research. She: “this way is faster”

  45. anthony avatar

    if cycling is so cool as you say why aren’t you doing it right now instead of writing about it?

    1. Because I like writing about cycling.

    2. Andrew Norris avatar
      Andrew Norris

      It’s all about doing the things you love, it is only cool if it suits you.

      1. Darren Darmanin avatar
        Darren Darmanin

        thank you for writing about it

  46. D.Jacob avatar

    …this is amazing. Thank You so much for doing this Tom!

  47. Thanks Tom.
    You are good in summarising all these considerations in a nutshell, as always.
    As for me, I’m still working on being able to think about nothing and accept that chance and chaos might take full control of my life. But, as time goes by, well, time goes by…

    1. Thanks Michael. I’m glad you consider a 5,000-word article a ‘nutshell’ 😉

      1. Andrew Norris avatar
        Andrew Norris

        It’s such a great read, time flies.

        1. 😀 Ooops, I meant compared to the three Lord of the Rings books (OK, I also got a version — in French — that came in six) you’ve already written, and soon the whole Mahabharata I’m sure…
          But it’s true: time flies, to such an extent that I didn’t have this sense of “length”.

      2. What an articulate, literate, honest and thoughtful article.

      3. Thanks Tom.…I think you convinced me I have to peddle to Patagonia; after traveling to Cuba, black ride, in 2000 I became that guy who sits bored listening…trying not to judge but failing.…at dinner to the mundane issues that privileged people find worthy to commiserate over. And, it is cringe worthy that there is a billion dollar Kardashian industry servicing and modeling that behavior.

        And, I have so many intellectual conflicts with my world that make me crazy, crazy is simply failing to model established social behavior and common social thought, and there isn’t enough time to be both honest, to reflect on and sort out the absurdity of American life, and, at the same time to be dishonest as a means to fit in with working peers.….or Americans.

        1. Forgot to punch the “follow-up” button. Thanks.

Something to add?