11 Travel Planning Mistakes You Don’t Know You’re Making

11 Travel Planning Mistakes You Don't Know You're Making

Our quest for the perfect trip: it’s never-ending. We’re brilliant travel planners—we fill spreadsheets with train times and oddly-spelled destinations, hawkishly watch airfares jump up and slide down, until one day we pounce. Months of diligence comes to the head, revealing in front of our eyes our eternal goal: the perfect travel plan.

But, eventually, even the mightiest travel planner falls.

Whether an experienced traveller or a first-time globetrotter, none of us are free from silly travel planning blunders. And you might not even know it. Next time you’re planning an epic adventure, keep your eyes peeled for these 11 travel planning mistakes:

1) Booking flights too far (or not far enough) in advance

Meet our travelling couple: Joe and Sally. Joe is a worrywart. He wants every detail planned, and wants it done yesterday. Sally, on the other hand, prefers to sort out details on the fly. Their trip isn’t for another 8 months: Joe wants to snap up his plane ticket now; Sally, at the last minute. Who’s right?


Abandoned Plane

A recent airfare survey shows that the prime booking time for the best airfare is 54 days in advance. That’s slightly less than two months before. (So much for minimalist travel planning!)

Keep in mind that 54 days in advance is an average. When flying to popular destinations—especially international—during high season, the longer in advance the better. (Think: Europe in the summer or tropical destinations on March Break or during Christmas holidays.)

Whenever you choose to book your flight, avoid the two-week window before departure. For most destinations, you’ll eat up a significant chunk of your travel budget purchasing last-minute flights.

2) Booking flights on the wrong day of the week

This one’s been out of the bag for awhile: experts claim that Tuesday and Wednesday are the best days of the week to book airplane tickets. It might not be entirely true.


While many airlines release sales on these days (with competitors soon following suit), snagging up one of these magical fares may require attacking the opportunity quicker than you might be prepared for. Often, these special fares are completely sold out within hours—or at least for the days you want to travel (funny how that works).

Prepare yourself to grasp that chance to book on the cheapest day with fury: set up daily fare alerts on Kayak and sign up for the promotional newsletters of every airline flying to your desired travel destination.

3) Not booking incognito

Ever notice that after searching for airfares multiple times they seem to go up, even in a matter of hours—or minutes? I speculate the answer to the question “Do airlines practice price discrimination?” is a clandestine secret that only a few tightly-lipped souls share. Until it’s proven let’s just follow this rule: eat your cookies before they eat you.

Laundry Ninja

When searching for and booking flights always use an incognito browser window to ensure that your browsing information isn’t used to jack up prices. Even if in the end the whole price-fixing speculation proves a giant misunderstanding, there’s no harm going incognito.

4) Ignoring layover times

Once upon a time airlines would refuse to sell tickets with short layovers. Airfare aggregators have changed that: now it’s up to you to figure out whether you’ll have time to disembark, rush through security, even clear customs or re-check-in, while sliding into the gate in due time for your next flight.

Rush hour

Always avoid short layovers—even if it’ll save you a bunch of money. Airlines don’t tend to be forgiving to travellers missing flights because of poor planning, and unless you’d like to be stranded in an airport—or spending money on an empty hotel room at your final destination and new plane ticket—it’s best to give yourself ample time between flights.

5) Not claiming your frequent flyer miles

Astute travel hackers know: claim your frequent flyer miles for every single flight. And what many travellers don’t realize is that you don’t necessarily need to fly the same airline every time to travel to benefit.

12 months of travel

The world’s two major airline alliances—Star Alliance and oneworld—cover the whole globe. Find out which airlines in each alliance fly between your home airport and your favourite destinations and sign up for one of the airlines’ frequent flyer programs. Even if you end up jetting overseas with a different partner in the same alliance, you can often request that the mileage be added to your account—even retroactively.

6) Improperly-sized backpack

It’s not always obvious until it’s too late, but a backpack that’s too big (or too small) can really take a toll on your body.

Backpacking Incan Trail - Machu Picchu Peru

A perfectly-fitting backpack can spell the difference between an enjoyable first walk in a city and a painful one. Be sure that your hip strap sits firmly on the pelvic bone and bears the weight of the pack when the shoulder straps are loosened. If the burden of the weight after adjustment still falls to your shoulders (or sits incorrectly on the the hip), it’s time for a backpack upgrade.

7) Sticking to “official” accommodation

Hostels, hotels, guesthouses, pensions—you’ve probably done them all. But besides these well-advertised and easy-to-book accommodation options there’s a whole whack of sleeping arrangements you may have never considered.

Apartment, Vancouver

From homestays to private apartments and couchsurfing to internet-café loungers, the possibilities beyond traditional accommodation are nearly endless. My new personal favourite: airBnB, where you can rent full apartments or private rooms for a fraction of the price of similar hotel rooms.

8) Letting your itinerary lead you

Does your travel planning look something like this: hop on a flight, land in a new city, spend one or two nights, hop on a bus, arrive in another city, spend one or two nights, and repeat?

It’s a common practice I’m all to happy to speak out against. (Time and time again.)

Atlas Mountains in Morocco

If you’re not a rabid destination-collector, I commend you; otherwise, here’s my most precious tidbit of advice: don’t let your itinerary command you.

Strike up a bit of a plan, a rough sketch if you will, but don’t follow it too closely. Travel has the power to surprise and bewilder only if you let it.

9) Relying too much on guidebooks

Just as your itinerary shouldn’t dictate your day, neither should a guidebook. As a starting point, guidebooks are fantastic: they decode an otherwise unfamiliar place and make it instantly accessible. But even when fresh off the press (which is not really so fresh) they’re also riddled with errors, and more importantly, omissions.

Where shall I go?

Guidebook writers don’t always have the luxury of time, sometimes writing with about as much experience in a place as our voracious destination-hopper above. Needless to say, there’s more to a city than a passing stranger—or even many bonafide locals—could uncover all on their own. Get out there and discover it for yourself.

10) Packing too much

I love airport baggage claims. (Well, at least as long as they don’t empty without my bag on them.)

Watching traveller after traveller risk a hernia to heave their 20kg+ bag onto the tiled-floor brings me some sort of weird amusement. An isolated case of schadenfreude, I guess.


Overpacking has to be one of the silliest of all travel blunders. Unless your planning to stay for a year—and even then, the ferocity with which some travellers pack is astounding!—try lightening up your load. Learning how to pack light is a virtue that’s well rewarded in better mobility and less pain.

11) Not learning enough of the local language

All of us are guilty of it: hoping English will be enough to get by. And yes—it is usually enough to get by. But we’re intrepid travellers. We want to experience more, don’t we?

chinese is hard

If you know where you’re going on your next trip well ahead of time, get out your phrasebooks and course books and try to nail down the basics of the local language. With even just a half an hour a day, you can make massive strides towards a more fulfilling and less frustrating trip.

Have you ever made any of these travel planning mistakes? I’d love to hear from you in the comment section below!


    • says

      Thanks, Phoebe :) Booking incognito is worth a shot. When I was searching for my flights to Helsinki last year, I noticed minor discrepancies myself within short-time frames that appeared to go away with searching incognito. It’s wasn’t exactly scientific, but it’s no harder than using a regular browser window. (Also, you don’t get those annoying re-targeted ads.) Let me know if you notice any difference!

      • leila says

        Hello Ryan….
        Informative article. Information re: incognito booking, as you I have researched only to come back within an hour and wa-la the fare has jumped. Would you PLEASE explain to me how I accomplish,,,,,incognito booking.
        Thank you,

        • says

          Could be just the dynamics of airline pricing (their official explanation for quick price hikes), but it would be a good time to test out the theory! To go incognito, go to the file menu of your web browser and click “New Incognito Window” or “New Private Browsing Window”. Not sure which browser you’re using, but most of them should have this setting (or something similar).

  1. Mark Tschirgi says

    Hey Ryan,

    I too wanted to say thanks for the incognito tip. I’ve never heard that before and will definitely look into it! Keep up the great work and I hope you’re well man. Cheers.

  2. says

    Great tips. I pretty much try to follow all of these. Although I only recently learned of incognito – I haven’t had a chance to check it out yet. I’m very curious to see the difference: I have a friend who swears by it. And good point about the layovers; always best to take the longer one just in case of delays or a super busy airport!

    • says

      And it seems that every airport is busy these days with all the new intense security measures! It’s so easy to miss a flight if you get caught in an immigration or security line-up. You definitely need more than an hour for bigger airports, especially if there’s any sort of delay at your point of departure (which, let’s be honest, happens a lot). Hope the incognito window can save you a little bit of money, Marsha!

  3. says

    Great tips Ryan. We do try to follow all of these as much as we can. Some just come natural for us like not relaying on travel guide that much, we never do because we like to discover things by chance and by ourselves. The only tips and advice we take sometimes is from locals, we value those more :)

    • says

      It’s funny how the more you travel the less you feel like you need to see. I totally agree: local advice trumps guidebook advice. I can’t think of a time I’ve been led astray by a local. In fact, I’d say nearly all of my most memorable moments have come from randomly discovering things, either on my own or through the advice of a stranger. Travel wouldn’t be nearly as interesting if it was all about seeing what we’re expected to see. I’m guessing that’s why not everyone falls in love with it like we have :)

  4. says

    Wonderful tips. I too often forget to book incognito, until I read a reminder like this. And 54 days is almost too far in advance for us, although would be a great goal to aim for.

    • says

      It’s split for me: sometimes it’s more last minute, but other times too far in advance (mostly when I’m in a panic because the flight prices are increasing by the day!). Since I travel mostly in high season though, I don’t think booking outside the 54-day optimum has come back to bite me too often. Constantly shopping around and knowing how much you SHOULD be paying to certain destinations at certain times of the year is really the best practice—and a super-nerdy hobby of mine! Thanks for reading, Rhonda :)

  5. says

    These are some really helpful tips and advice. I never bothered to find out when is the right time to book a flight. Setting alerts for cheap flight offers is wise. It may save a lot of money!

    • says

      Indeed! I’ve literally saved hundreds by pouncing on daily flight alerts. If you have a smartphone, the KAYAK app is great for that: it will send a push notification if someone else finds an awesome deal for your destination on your dates. Love it!

  6. says

    These are very true! I’ve found that flight prices are cheaper on some websites on Tuesdays compared to the weekends when I’ve been searching, same for car insurance too haha. I remember travelling in Vietnam and using a guidebook all the time – it’s the only place where I’ve used one so much and I think an over reliance on travel guides definitely starts to kill the fun.

    • says

      Even if it only saves $10-20, it’s worth it! I really enjoy reading guidebooks still, truth be told, but tend to do it more as an introduction to a place I’m completely unfamiliar with while sitting at home rather than using it to plan out every day while I’m on the road. You’re right though: it does kill the fun if you’re spending every day with your face buried in the book, hopping between their recommendations.

  7. says

    I always fear these types of posts because many people when they write about travel mistakes, they often take on my beloved fanny pack. Glad to see the fanny pack did not draw any ire here and there were many good tips. I love the erase cookie suggestion when searching for flights.

    • says

      If anyone pulls off the fanny pack, it’s you Ted! I’m not running a fashion site and don’t feel at all qualified to comment on what a traveller should wear. If I ever do, please remind me of this conversion :)

  8. says

    Great tips Ryan. Unfortunately travelling with a toddler means mine and my wife’s packs are pretty full. However we’ve both been slack at learning the local language, but we’re stopping in France for a while so am learning via the Duolingo App. Here’s hoping it helps :)

    • says

      Yeah, not much you can do about lightening the load there, Chris! I can only imagine how much heavier travelling with a toddler would be. I can really relate there: I’m often far more motivated to learn the language on a second trip than the first, and I can honestly say that most of the time, it would have made the trip much much better knowing even a tiny bit beyond the basics. Best of luck in learning French with Duolingo, Chris! I’d be interested to hear how you make out with it. Keep in touch!

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