Carryon Packing: The illusive Art of Packing your Carry On and the 10 Ways I Utterly Failed at it

May 19, 2017

I Hate Carryon Packing

Okay, I’ll admit it. I love traveling but I absolutely hate carryon packing. I mean if it was a choice between a root canal and packing I might actually choose the root canal. That’s why I usually just throw all my stuff in my checked luggage and let the baggage handlers deal with the catastrophe that is my suitcase.

The ultimate list of carry on blunders.

However, my packing plans changed when I brought my rolling bag to Sweden with me. It was a real big pain in the butt, and by the end of the trip, I literally felt like I was dragging an entire rock quarry around with me (And my back kind of hurt because I’m old like that. Hello sponge baths and tapioca pudding). So, to avoid this particular annoyance, I decided to be a “travel baller” and fit everything, for my trip to Greece, in my nifty, super new, carry on backpack (I know I’m a traveler because I never shop for shoes. I always shop for new backpacks. You should see my amazon search history).

Well, needless to say, I am not a carry on packing aficionado. I mean, I always put my liquids in my checked bag, so I didn’t even know that they needed to be in clear bottles that are inside of a clear Ziploc bag (I’m probably the only person on Earth who didn’t know this. Hello captain oblivious).

Therefore, it should come as no surprise that I made a few mistakes when packing my carry on for my upcoming trip to Greece. And let’s be honest, if you’ve read my blog then you know that my mistakes are usually pretty hilarious. So, here is a list of my biggest packing fails,  not only for your amusement but so that you  can avoid making these mistakes too (Until this very moment, I never understood how much of an art form packing is. But it is and I am not that artistic).

1. I just spent my entire vacation budget in CVS (Oh the shame and humanity)

Avoid spending all your money at CVS when packing your carry on.

Ummm… I don’t know how it happened. I just went to CVS for a few travel size items, and left with a bill for what felt like $10,000. How does this happen? I only bought little travel size bottles of shampoo at $3.99 a piece! I mean sure, they are like a tenth of the size of a regular bottle of shampoo, and like the same price, but they were so cute and little and were in the travel section, so I just had to have them. I guess I just won’t eat for a few days on my trip (Just kidding. I turn into a psycho when I don’t eat).

2. I just spilled half of my travel-sized products while transferring my liquids into clear bottles.

Seriously, what kind of magical powers do you need to transfer shampoo from one bottle to another? I literally tried to MacGyver a funnel out of an old business card and failed miserably. All I got was a hand full of suntan lotion and a mess on the floor. I even tried to practically milk the bottle but to no avail. I actually got more sun tan lotion on the ground than I did in the clear plastic bottle. Now I’ll have to go back to CVS and spend the GDP of a small island nation, just to make sure I don’t sizzle like bacon while I’m away.

3. Wait, I need to hitch a ride to the airport?

Because there are no great public transportation options available to me (Stupid suburbs of NYC. This fact irks me so.), I always have to bum a ride to JFK airport. I mean I would take a cab but it costs about a $100 (and the last time the guy was rude and there was no AC, in the middle of the summer, and we got stuck in traffic. Clearly I am not doing that again.) So since I am not independently wealthy, I now need to beg someone to drive me to the airport. I usually try to bribe my friends by giving away my first, as yet unborn, child. But shockingly, I don’t have any takers.

That’s when I know I have to start crying to my family or selling my soul to the highest bidder (hopefully I can keep my soul but it is so hard to find a minion to shuttle me around these days). I mean it’s so bad that my dad even said he had a “colonoscopy”. Yeah, okay dad. Whatever you say (He actually really did. LoL). But seriously, anyone? Bueller? Bueller?

4. More electronics, more problems.

So, I am not super fancy at all. I mean, before I became a travel blogger, I didn’t even bring a camera on my trips, let alone a laptop or a tablet. I would rock out with my iPhone and take, what I thought, were Ansell Adams caliber photos. Well, times they are a changing. My phone will no longer suffice, so I forced myself to buy a tablet and a camera. This way, I can still take pictures and write while I travel (You know you wouldn’t be able to function without more riveting stories like this one. LoL. I mean seriously, what would you do for ten whole days?) .

But I am just overwhelmed by all the USB cables and chargers and electronic paraphernalia. I feel like I am going to forget something or like I need a portable power plant to help me manage all these wires and charge all these devices. Makes me want to run away and hide in my blanket fort (I know, super adult of me.)

5. Adaptor Mayhem

Avoid charger mayhem when packing your carry on. Get a single adaptor and convertor in one.

This is the worst. I never know if I need an outlet converter or a currency adaptor or both. I literally just had to spend an hour on Amazon trying to figure out exactly what I need so that I don’t blow up all my brand new electronics. Maybe I should just hire a personal scribe and photographer. Either that or I’ll just hire a carrier pigeon and call it a day (And don’t even get me started on the wireless cell phone chargers that I have to bring. At this point I should just use all my electronics to revive the entire radio shack franchise. #careergoals)

6. Pills, pills, pills

Geez. I never realized how many vitamins and medications I take. I tried to put all these pills in one giant Ziploc bag but then I look like a total drug mule. Seriously, if someone sees that bag they are going to ask me if I am preparing for a guest role on Narcos. But if I bring all the bottles of vitamins and medications, then I’ll have to vacation naked because there will be no room for my clothes.

Oh the dilemmas that we face in life. Maybe ‘ll just throw them into little separate bags and hope no one notices. I’ll be like, “Hey guys. Nothing to see here. Just killing it with my secret stash of B-6.” Yeah man. I live hard, carpal tunnel syndrome hard.

7. So much Netflix and so little time.

This is by far the HARDEST and MOST IMPORTANT packing decision I have to make, and I am failing miserably. I mean, now that Netflix let’s you download shows, how do you decide what to download? Download too little and you run out of things to watch. But download too much and you won’t have enough storage for photos. The struggle is real my friend. I am going to have to make some tough choices. My sanity while flying depends upon it.

When pavking your carry on, avoid buying three other pieces of luggage as well.

8. I can’t stop buying luggage that I don’t need (Make it stop)!
Hi guys. My name is Kelly and I have a luggage shopping addiction. I mean purses, pssh. Who cares. You just use them on a daily basis. No big deal. But any travel related baggage, that I only need on vacation, and I am all about it. I mean, for this trip alone, I am sad to say that I bought three different bags, all of which I don’t need. But I saw some of them on your blogs and just had to have them. I want to look super cool like all my fellow female travel bloggers.  I seriously have visions of backpacks and rolling Samsonite carry-ons dancing through my head. The only way this could get worse is if I get my new bags all scratched and dirty on my first trip (You know that’s going to happen right? I’m totally going to spill coffee all over them and ruin it all. But then I’ll have to buy more…).

9. Contact Confusion

I am the worst when it comes to packing contacts. I mean, first of all I need a special contact lens solution because otherwise my eyes will have an allergic reaction and burn like the surface of the sun. I also never know how many contacts to bring. I mean, my monthly contacts are expensive, so I don’t want to bring too many and lose them. But if I bring too few, then I’m gonna have to walk around in  glasses and look like a frumpy librarian (No. When I wear glasses I do NOT look like a cute hipster). Does anyone else suffer from these mundane carry on problems? Because I am over here making this into a United Nations level problem when this contact controversy is more like a luxury first world problem. Sigh. Big sigh.

10. Guidebook Guru FAIL

A guide book may not be as useful in your carry on as you think. Check out my guide to Athens here instead. While you’re at it, find out all about the Acropolis here.

So, for my upcoming trip to Greece, I was trying to be all responsible
and buy a guidebook so that I would actually know where I’m going and what I’m doing. Well, that worked out great, until a few of my friends informed me that the information in my guidebook was outdated and basically just WRONG.

Awesome. I just wasted $20 on a book that has inaccurate information. But I can’t return it and feel like I have to bring it on my trip because I paid for it. Besides, what if I really do need it for something and end up in another country because I don’t have it (You laugh but it could happen. Okay, maybe not but you get the point)? Talk about an outdated guidebook nightmare (I even tried to get the most recent edition but it was still incorrect). Just go on the internet. Websites never lie (wink, wink).

Moral of the Story

Learn from my mistakes and don’t make these epic  fails when packing your carry on!!

Looking for a great carryon bag? Check out some of the carryons that I use when I travel.

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Nanny by day and travel blogger any other time.

I love writing and traveling and bearing my soul on the page.
I want to inspire others to face their fears and join me on an adventure.


  • Dariel 10 months ago

    You are hilarious!! I can totally relate regarding the contacts, always have to count and think and count them again lol. You just made my day girl 🙂

  • Minna 10 months ago

    I feel ya girl! My SO has TWO toiletry bags full of pills in the bottom of his bag because I packed for every eventuality. So far all we’ve used is the ibuprofen because his back hurt from carrying the backpack… said backpack is also full of all of my camera/blogging/tech stuff. I’m carrying my own clothes and journal…

  • Rhiannon 10 months ago

    I love when you update your blog, it’s the highlight of my day. I have always been a suitcase person (plus a carry on) cos I’m probably the worst over packer on the planet. Especially since I literally wear the same shit every day, why do I need 5 different shirts? Please, tell me. I loved all of these, especially the pills one! I’m always bringing so many, just incase I get a headache, or a life threatening disease that only every type of pain killer will cure. UGH.
    Anyway, I hope you had a rad flight to Greece, and please, take lots of photos! Greece is definitely in the top 5 on my travel bucket list. 😀

  • Becky 10 months ago

    Ha ha so funny Kelly. My name is Becky and I am also a bag addict. Rucksacks mainly but any new bag for my trip is so tempting!!!

  • Sara 10 months ago

    Haha your misadventures in packing just made me actually laugh out loud. Totally feel your pain though. I am the worst. Loved this read though, thanks for sharing!

  • Julia Dent 10 months ago

    I am the WORST at packing carry ons, and I somehow recently made the mistake of having my backpack over the weight limit!! I just need someone to carry all my stuff. Also, did you get a Fjallraven in Sweden?? 🙂

  • Courtney Jones 10 months ago

    Okay, there is so much of this I relate to! Spending WAY too much money on mini shampoo? Check. Obsession with luggage? Also check. Choosing how many Netflix episodes to download? Triple check. Hilarious read – the struggle is real!

  • Brenda 10 months ago

    Girl! Next time you should hire me for this! LOL! Most of the time they dont make a big deal if the liquids are in clear bottles or not, but, I learn a magic trick that’s absolutely a lot better: shampoo and conditioners bars and solid toothpaste. The less amount of liquid possible!

  • Alyssa J 10 months ago

    Haha I feel you! I had the same mistake on my first few trips but after awhile you’ll get a hang of it! :p

    I personally have a TSA friendly ziploc bag where I keep all of my travel essentials (makeup, liquids etc) and just keep it there even when I’m not traveling! Saves time, plus you can just grab and go on your next trip! Also with toiletries I would recommend going solid – a bar of soap instead of shower gel, solid shampoos instead of liquid and etc!

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