20 Travel Packing Hacks & Mistakes I Learned the Hard Way

You should know, I pride myself on being an excellent packer.

I was doing the carry-on only thing way before it was cool (aka before the airlines started charging for checked baggage). I can pack fast and light.

I once packed for 3 weeks in just a school backpack, on a trip that took me from the cold city streets of London to the desert of Morocco in February!

So I’ve definitely learned my fair share of travel packing hacks over the last 15+ years of travelling independently. But sadly, I had to learn most of those hacks the hard way by making some big packing mistakes.

Turns out, I’m not the perfect packer. Despite moving houses close to 40 times in my life and travelling to almost 50 countries, I do make packing mistakes.

Below I’m sharing my best travel packing hacks, tips and mistakes to avoid based on my many years of schlepping suitcases, backpacks, purses and duffels around the world.

Disclosure: Some of the links below are affiliate links, meaning if you click through and make a purchase, I will earn a small commission at no additional cost to you. Thanks for your support!

1) Don’t pack jeans

I’m starting off with a controversial one! I know some people love jeans. They are into their denim and sport jeans every day of the year.

I am not those people. I think jeans are uncomfortable. I own a few pairs and will wear them only when I have to.

I would much rather wear leggings, joggers, slip-on pants, dresses or skirts. I’m all about the elastic waistband (this probably tells you a lot about me).

And you know when I really hate wearing jeans? When I have to sit on a train for six hours in a single day or when I’m trying to eat my weight in French pastries.

Not only are jeans horrible to wear on a plane, train or long car ride, they’re super heavy in your bag. They take up a ton of space and weight.

And if your jeans get wet, they’re even more disgusting. On a trip to London in 2018, I made the mistake of wearing jeans on a day that absolutely poured. I was soaked through and my jeans didn’t dry for many hours after the rain stop.

I definitely regret packing jeans on that trip. As soon as we got home, I went out to buy some non-jean pants which I’ve exclusively packed for future trips.

2) Pack layers

This is an oldie but a goodie: Pack layers! Rather than only packing tank tops or only packing huge coats, you need layers of in-between items for in-between weather.

For some reason, I completely forgot about this cardinal rule on a trip to Europe in the middle of October. I didn’t have a single cardigan or light sweater with me, just a rain jacket.

Cut to me buying a super soft cardigan at Primark a few days into our trip because I was freezing. I know sweaters are bulky, but I do suggest packing a few light sweaters or cardigans if you’re doing any shoulder season travel.

Layers are great because they take up less space than big heavy items and allow you to dress for whatever weather you’re served.

Even if you know that Sedona, Arizona is going to be shorts and t-shirt weather, you may still need a light sweater for night time or hanging around your accommodation (which is how I ended up with my new favourite black sweater from Target!).

3) Prepare for rain

Unless you’re headed to a desert, you should count on getting at least a small bit of rain during your travels. And if you’re going somewhere notoriously rainy, like my hometown of Vancouver, you definitely need to prepare for rain!

For years, I struggled with this. I’d pack a rain jacket, but my feet would still get wet. I’d pack an umbrella, and end up not using it (like when I miraculously got only sunny weather for a week in the UK in January!).

My new favourite travel packing hack for rainy days? Vessis! If you haven’t heard of them, Vessis are waterproof shoes that are breathable, light-weight and attractive enough for walking around a new city.

The great thing about Vessis is because they’re so versatile, you can wear them rain or shine. So you don’t have to pack an extra pair of shoes for rainy weather (that you would inevitably forget to wear on the day it actually rains anyway).

I’ve been wearing the Weekend style Vessis for a few years now and I absolutely LOVE them. They’re my go-to shoe for everyday life in Vancouver and also whenever we travel. This isn’t sponsored; I’m just a big fan!

(Though Vessis, if you’re reading this, email me!)

I’ll still pack a rain jacket if the weather looks particularly bad, and pack or purchase a lightweight umbrella, but at least I don’t have to worry about my feet getting wet.

The grossest feeling is walking around all day in wet socks and shoes. With Vessis, that’s not a problem!

4) Choose your footwear carefully

These days, I pretty much only pack my Vessis for trips unless we’re hitting the beach (add flip flops), going to a wedding (add flats), or going back to Toronto for Christmas (add winter boots).

But before I found Vessis, I made a lot of packing mistakes when it came to my footwear. I’ve literally thrown out shoes mid-trip because they were falling apart (bad sneakers on a glacier in Iceland will do that to you!).

I’ve also made the mistake of packing too many shoes. In my opinion, you never need multiple flip flop options for a trip – one pair will do!

I understand that certain trips really do require a large number of shoes. If you’re hiking Kilimanjaro before relaxing on the beach in Zanzibar, I can understand why you may need 4+ pairs of shoes. But if you’re just going to Italy for a week, you can probably get away with 1-2.

I recommend focusing on getting a really good pair of everyday shoes. Shoes that are comfortable, fit the vibe of the locale and match with most of your outfits.

Buy these shoes in advance so you can break them in. You don’t want to discover on day one of a three week trip that your new shoes give you blisters. C’mon, that’s a rookie mistake.

Then throw in one or two other pairs of (hopefully light-weight) shoes that serve a specific purpose. So hiking shoes if you’re going hiking or flip flops if you’re going to the beach. Not another pair of runners “just because.”

5) Switch to an e-reader

This one is for my bookish travellers. I’ve been singing the praises of an e-reader ever since I purchased one for myself in May 2019. My Kobo (similar to a Kindle) is one of my favourite purchases ever.

I know some readers turn their noses up at ebooks read on screens but let me try and convince you with five very good reasons to pack an e-reader on your next trip:

• E-readers are lightweight. No more lugging huge books around with you! You can slip this in your purse or day bag.
• E-readers can hold tons of books. No need to narrow down your favourites, get stuck with a book you don’t want to read or pack heavy extra options just in case.
• E-readers allow you to read in the dark. This is super handy on planes, trains or when the jet lag hits and you don’t want to wake everyone else up by turning on the lights at 3am.
• E-readers allow you to read books in your native language. If you were planning to pick up new books along the way, you might not be able to find a great selection in your language depending on where you are.
• E-readers are affordable. Yes, there’s the up front cost to buy it but you can buy one second hand for much cheaper and then borrow digital books from the library for free!

Have I sold you on an e-reader? Seriously, they’re the best! The only reason I’ve been able to get back into reading more as an adult has been thanks to my e-reader and reading on trips.

6) Switch to digital instead of paper

It probably won’t come as a surprise to you that I love to research and plan trips, resulting in lots of spreadsheets, documents and yes, even slideshows.

For way longer than was technologically necessary, I would then print those documents, tickets and confirmations resulting in a huge dossier of travel documents. It got to the point where this folder of paper was a few inches thick (and heavy!).

Sometimes, it’s important to print things out. Some attractions actually require a paper ticket or some destinations really don’t have wifi.

But nine times out of ten, you don’t need a print out. Hotels don’t even ask for your confirmation anymore or, if they do, you can just pull it up on your phone. Everything is digital or has an app these days.

So, join me in the 21st Century. Embrace the Cloud and say no to a million print outs.

7) Bring a day bag

When I travel carry on, I usually have my big backpack and then my purse. If I’m bringing my laptop, I’ll put it in its case and put that in my big backpack.

Which means, I sometimes forget to bring a day bag. A day bag is, as you probably guessed, a bag you take with you on a regular day out exploring. It’s small, easy to carry and holds everything you might need for the day.

Some people get away with just using a big purse as their day bag, but I like to have my little cross-body purse when I travel (and in my daily life). It’s light-weight and harder to steal from.

But sometimes you just need a backpack, tote or duffel for the day! This is where you’ll store snacks, a water bottle, an extra sweater and your e-reader – all of your essentials for your day’s adventures.

In the past, we’ve ended up buying bags mid-trip just so we could stop shoving my purse and Colin’s pockets full of things we needed. But finally, we’ve smartened up and started packing a day bag from home.

8) Pack a few snacks (that you’ll actually want to eat)

I’m a huge proponent of eating local food. In fact, it’s one of my favourite parts of travel.

But I also believe in packing snacks. I don’t think you should pass on the Pad Thai in favour of a granola bar, but I do think a granola bar can save you in a pinch if you sleep through your flight’s meal service or get stuck on a long train ride.

After going to bed hungry a few too many times when I showed up to a city late and all the restaurants were closed, I’ve finally learned to pack some snacks. Unfortunately, I still make the mistake of packing bad snacks.

Some bad snacks are obvious. You can’t bring things that are going to disintegrate, get moldy or take up too much space. But other bad snacks are harder to detect.

A bad snack that trips me up is the aspirational bad snack. “Well, of course I’ll be the type of person who loves to eat sugar-free dried fruit and nuts when I get peckish abroad,” I think to myself.

But that’s not true. I like my dried fruit covered in sugar and my nuts covered in chocolate (or preferably, just the chocolate, hold the nuts). So learn from my mistake: If it’s not a snack you reach for at home, don’t pack it for the road.

9) Go carry-on only

I know this is controversial but I am firmly on Team Carry-on Only. I recognize that carry-on only travel isn’t an option for everyone but if you have the ability, I promise you won’t regret it.

Here’s why carry-on only is amazing:

• It’s cheaper. No checked baggage fees for you.
• It’s faster. You don’t have to arrive early to check in bags or wait forever at the baggage carousel to collect them.
• It’s safer. There’s no risk of the airline losing your luggage when it’s right beside you the whole time.
• It’s easier. You are much more mobile when you’re not lugging a 50lb case behind you down cobblestone streets.

To which you might be thinking, “Sure, that all sounds great. But how am I supposed to get six weeks worth of clothing into a carry-on?”

To which I’ll answer, “You’re not.”

You don’t need to pack for six weeks or even six months. You need to pack for 1-2 weeks and plan to do laundry.

Laundry is almost always going to be cheaper than checking a bag. And it’s available pretty much everywhere around the world.

I understand that sometimes checked bags are better. We checked bags when we moved to Prague for a year and once on an all-inclusive trip to Mexico because it was free (though my husband, Colin, ended up with his bag lost for 5 days and having to wear resort-branded clothes, so it maybe wasn’t worth it for him).

But most of the time, carry-on only is the way to go. Even if you’re travelling through different climates or will need different footwear, you’d be amazed at how much you can pare down and how much you can fit in a carry-on.

10) Start a packing list on your phone

This is one of my favourite packing hacks because it’s so simple and underrated, yet so useful.

Most people either pack way before a trip or pack at the very last minute. But both of these options have flaws.

If you pack too early, you end up having to take things out as you need them in your regular life. I don’t know about you, but I don’t own enough socks to have 10 pairs just sitting in a suitcase for weeks.

And last minute packers struggle to get their bags packed in time, often stressing themselves out and forgetting crucial items at home.

So how do you avoid this? By starting a packing list!

In the notes app of my phone, I create a packing list a few weeks before my trip. Every time I think of something I don’t want to forget, rather than packing it away while I still need it, I just write it on my list!

If you’re not sure where to start, check out this 2 week trip packing checklist.

11) Don’t pack your maybes

Whenever I start packing clothes for a trip, I put them into two piles: definitely coming and maybe coming. The idea is that if I have room at the end, I can add in the maybes.

And almost every single time I toss in a maybe, I don’t end up wearing it.

If you’re not sure if you should pack something, you probably shouldn’t. When you’re trying to pack light, you don’t have space for something you think you might wear.

This doesn’t just apply to clothes. This goes for books (though if you’re using an e-reader like I suggested, this isn’t a problem), shoes, tech gear, accessories and anything else you might be packing.

Trust that the tiny voice in your head saying, “You probably don’t need this,” is right. And, even if the voice is wrong, you can likely pick up a replacement item wherever you’re going.

12) Make sure you can mix and match your clothing

As someone who lives in leggings, I probably shouldn’t be giving out fashion advice. So rather than telling you what must-buy items should be in your capsule wardrobe, I’ll simply say: make sure it’s all mix n’ match.

By that, I mean that most of the tops you’re bringing should be able to pair with most of your bottoms. That way, you can create different outfits and get more wears out of each item.

If you have a shirt that only works with one pair of pants, leave it at home. You won’t be able to re-wear it on your trip, which is key if you’re packing carry-on only.

Some people say it’s easiest to mix and match if you stick to one colour palette or if you only wear neutrals. But I’m not here to tell you to leave your fabulous, colourful, patterned outfits at home!

I brought a bright red dress on our Southeast Asia trip. It was the farthest thing from neutral. But it covered my knees and shoulders, was breathable and comfortable, and popped against the green and stone backdrop, making it the perfect option for exploring Angkor Wat.

13) Don’t leave home with a full bag

I always worry when I see people squeezing, squishing and sweating over their bag as they take off for a trip. If you leave home with a completely full bag, you’re going to be in trouble coming back!

Your bag at home is the most organized and neatly packed your bag will be all trip. After this, it’s going to be rushed packing jobs as you hurry to check out on time or packing in dimly lit, tight quarters after a long day of sightseeing.

Plus, if you’re like most travellers I know, you’ll want to buy something while you’re abroad. Where do you plan to put your souvenirs if your bag is already stuffed full?

That’s why I highly recommend leaving a bit of space in your suitcase when you leave home. That way, you have room for a few souvenirs or a clumsy repacking job.

PS: If you’re naturally a heavy packer or like to shop while travelling, I recommend investing in an expandable suitcase. Plus, most extra large suitcases offer multiple compartments to help you organize your items, which will make packing easier.

We recently started using LEVEL8 suitcases and have found them great for fitting in lots of things and smooth for rolling along city streets and airports. Get 10% off your LEVEL8 bag with my code, TEASPOON10.

14) Use packing cubes

Here’s another packing debate where people feel pretty divided: to packing cube or not to packing cube? As for me, I’m a big fan of the packing cube.

I love packing cubes for their organizational abilities. Especially when you’re throwing everything into a backpack, it’s really nice to have one cube for tops, one for bottoms, one for undergarments, etc.

Packing cubes can be used to divide up dirty vs clean clothes, separate shoes or even organize your tech so you don’t have a million cords and chargers floating around your bag.

They’re also great if you’re moving around often and don’t want to fully unpack. Sometimes if I know I have an early train to catch, I’ll put my next day’s outfit in a packing cube so I can easily grab just that cube when I wake up.

I haven’t tried them myself, but I like the sound of compression packing cubes. Not only do these keep you organized, but they also save you some space!

15) Roll thin, fold thick

There are two people in this world: Those who roll their clothing and those who fold (or flatpack) their clothing. Choose your side wisely.

Personally, I think the best approach is a bit of both.

In my experience, rolling works best for thin items, like t-shirts and underwear. Whereas folding is better for thick items, like jeans and sweaters.

Thin items roll well and I do find it’s easier to fit more of them into a packing cube when they’re rolled.

That being said, rolling does take more time. I’ll often roll on the way there and not bother on the way back. Rolling can also leave your clothing kind of wrinkled.

Thicker items don’t roll as well. I find when I roll up sweaters, they actually take up more space as they’re trying to escape out of their tight roll. So for these, I prefer to fold.

16) Bring a scarf

A scarf is the ultimate travel item because it’s so universal. I try to pack one everywhere I go (except that time I left my scarf on the train to the Blue Mountains in Sydney).

A scarf can be used when it’s chilly to keep you warm or as a fashion accessory to mix up your outfits. It can cover your shoulders when you’re temple hopping or be made into a skirt for beach bar hopping. You can easy use a scarf as a picnic blanket or beach towel.

See? It’s universal!

17) Bring bags

I’ve already talked about bringing a day bag, but there are a few more bags I think you should pack along with you.

Bring along a few Ziploc/sealable bags of different sizes. These are great for storing liquids and toiletries or small items, like jewelry. You can use them to wrap up opened food or hold wet things, like a bathing suit you didn’t have time to dry.

I also recommend packing some reusable bags. These are awesome if you want to hit a local market or grocery store, or if you need an extra day bag. Colin and I often designate one as our snack bag, making it easy to bring our snacks along from place to place.

And, reusable bags work great as laundry bags!

18) Wear your heaviest outfit

This is an oldie but a goodie when it comes to packing hacks: Wear your heaviest clothing and shoes on travel day.

By wearing your heaviest outfit, you avoid putting it in your bag (duh!). That means more space and less weight in your bag. The airline may weigh your bag but they won’t weigh you!

Of course, you still want to be comfortable. I don’t recommend forcing yourself into three pairs of pants, two sweatshirts and snow boots just to keep your bag weight down. Remember, you still have to walk around all day in that outfit.

But if wearing the boots is more comfortable and less heavy than carrying them, then go for it!

19) Know where your essentials are

If you took my previous advice to travel carry-on only, then you have the comfort of knowing that all of your stuff is with you at all times. But even then, it’s important to know exactly where your essentials are located and how you can access them.

For example, if you have to take medication, designate a specific spot for it in your bag that you can easily get to. You don’t want to be tearing your suitcase apart every time you need your meds.

If you know you’ll want your e-reader, headphones and Glossette raisins at your seat with you during the flight (my personal flight essentials), put them in an easy to access pocket so you can quickly grab them before putting your bag in the overhead compartment.

This goes for your liquids and electronics too. If you’re flying through an airport that asks you to remove those items from your bag during security, you don’t want to be that person who’s holding up the line trying to find that one lotion you know is floating around your suitcase somewhere.

20) Know the rules

Speaking of security lines at airports, you also don’t want to be the person who gets their full-sized shampoo bottle taken away because you didn’t know about the liquid limit.

While the rules are changing (some airports don’t have a liquid limit anymore!), it’s important to do your homework and learn the rules for your trip.

What size and weight bag can you bring? Are liquids allowed? Do you have to take your shoes off and electronics out for the security line?

If you’re not an experienced traveller, I think it can be very comforting to do some research ahead of time. It can also save you a lot of headaches (and excess baggage weight fees!).

For more packing hacks and travel tips in general, check out my travel tips post!

Wrapping up my travel packing hacks, mistakes and lessons learned

While I stand by my 20 packing tips above, I don’t get it right every time. Even though I’m an experienced traveller and packer (I’ve moved house over 40 times!), I still mess it up.

That’s why I think the most important packing hack is to just keep things simple. You don’t need every fancy packing contraption out there to ensure everything you own is theft-proof, compressed or USB-chargeable.

Don’t stress yourself out trying to put together the perfect packing list or ensuring you’re optimizing everything to max efficiency. Prioritize simplicity. How can you make packing, and your trip, easier on yourself?

For me, that means a light bag that I won’t hate dragging through the streets of a foreign city. It means easily accessible items that are well-organized. And it means having a few trusty items, like Ziplocs and granola bars, just in case.

The wonderful thing about packing mistakes is that most are very fixable. There’s a good chance you’ll be able to buy whatever you forgot wherever you’re going or ditch a few items if your bag is too heavy.

Plus, with every trip you take, you become a better packer. You’ll know what you need (and what you don’t), how you like to carry it and when you want to pack it.

So fret not, my packing proteges. If you’ve made it this far, you’ve likely consumed all of the packing knowledge you need. Start filling that bag and focus on what really matters – your awesome trip!

I’d love to know: Do you have any favourite packing hacks? And for baby-specific packing hacks and tips, check out my baby essentials travel packing list!

Need more travel tips? Check out these posts:

• Travelling Alone for the First Time? 11 Solo Travel Tips
• Fast Travel VS Slow Travel: Which Is Better?
• How to Plan a Trip to Somewhere You’ve Already Been
• 21 Popular Travel Items You Don’t Actually Need
• Should You Travel with Debt?
• How to Choose Where to Go on Your Next Trip
• What to Do When You Hate a Place