How to Be a Terrible Traveler: My Top 8 Tips

by | Nov 11, 2019 | USA | 22 comments

A few nights ago, lying sleepless in bed due to jet lag after my 26-hour journey from the United States to South Africa two days before, I had a profound realization: I am a really terrible traveler.

Sunrise at Dulles Airport in Washington DC
Sunrise at Washington Dulles Airport. (Note: All the photos in this post were taken on the fly with a smudged iPhone lens.)

“How can Heather be a terrible traveler?” you may be asking. I often ask myself the same question.

Nine years ago I chose to move across the world, knowing it would mean a lifetime of transatlantic travel. Then I became a travel writer. I travel all the time, for a living no less. And yet I’m terrible at it. I get worse and worse every year.

My nephew Jack runs blithely through the quiet airport in Burlington, Vermont. If only he knew the decades of terrible traveling that await him.

Would you like to be a terrible traveler too? It makes for great conversation. Just ask my friends and family who have the privilege of listening to me moan about traveling — for weeks or even months before, during, and after my annual pilgrimage from South Africa to the United States and back.

Just in case, here are my top eight tips for being a terrible traveler.

Terrible Tip #1: Don’t Make a List

Packing lists are for sissies. Why plan when you can just wing it? Throw a bunch of clothes into your suitcase a couple of hours before the flight and hope for the best.

Packing without a list results in exciting, unexpected outcomes. For example, you might pack two sets of flip-flops while forgetting your leather clogs, even though you’re traveling for four weeks through multiple winter climates in which flip-flops are unnecessary and clogs are totally essential.

You may then find yourself trudging the streets of Washington D.C. — one of the most expensive cities in America — on the first day of your trip, searching for a suitable leather clog replacement that won’t blow your shopping budget. Thank goodness for DSW.

Terrible Tip #2: Take a Huge Suitcase

Why travel light when you can travel heavy? Bigger is better. Take the largest suitcase you can find, just to make sure you’ll have plenty of space.

Jesse the car sleeping on Heather's suitcase, which she brought because she is a terrible traveler.
Bonus: Large suitcases double as comfy cat beds. Just ask Jesse, feline resident of Westminster Street in northwest Washington D.C.

Never mind that bigger suitcases are heavier than smaller suitcases, even with nothing in them. And never mind that a big suitcase filled to capacity will probably surpass the airline baggage weight limit, resulting in manic swapping of heavy and light items between checked and carry-on bags while a bored airline agent regards you with disdain.

On an epic journey like mine, which included five different flights across America and the world, you’ll have to repeat this exercise multiple times. Yaaaay. It’s all part of the terrible traveling adventure.

Terrible Tip #3: Neck Pillow? I Don’t Need No Stinking Neck Pillow

Many frequent travelers use neck pillows to make themselves more comfortable while trying to sleep on long-haul flights. I say: Why bother? Neck pillows take up space and my carry-on is already overpacked (see Tip #4).

Plus I tried to use a neck pillow once, in 1995, and I didn’t sleep a wink. Waste of time, I say. Also neck pillows look very uncool.

I’d prefer to toss and turn uncomfortably in my seat for the duration of my 17-hour flight, failing miserably to sleep so I have an excuse to be tired later. Fun!

Terrible Tip #4: Overpack Your Carry-on

Ever noticed a traveler step onto the plane with nothing but a briefcase or a handbag flung over her shoulder? Boring.

Why pack a small, sensible carry-on when you can rather stuff every precious item you own — oversized laptop, two cameras, four lenses (including that heavy 70-300mm you never use), and a couple of large books (even though you also brought a Kindle) — into a large, heavy backpack?

Fill that backpack to its breaking point. Stress out at the check-in counter, knowing South African Airways has an eight-kilogram weight limit for carry-on bags and yours is definitely 12, maybe 14. They hardly ever make you weigh it but every once in a while they do…Gotta love the anticipation.

Proudly be that person who everyone else hates in the American airport security line: the one who needs at least five plastic bins for all her many electronic belongings that must go separately through the X-ray machine due to tedious TSA air travel regulations.

“Whose bag is this?!” yells an angry TSA agent, dangling an unwieldy backpack from her hand. “I need to run it through again.”

Own it: That backpack is always yours.

(This tip does not apply in South Africa, where airport security is infinitely more relaxed than in America.)

Airport security at Denver airport
The airport security “line” (a.k.a. clusterfuck) at Denver Airport.

Terrible Tip #5: Shop Excessively While Traveling

I normally hate shopping. But I love to shop while traveling, which is great because it creates thrillingly complex packing scenarios. A new cowboy hat from New Mexico? Yee-haw! Cowboys hats are impossible to pack so I’ll have to wear/carry it through 30 hours of flying/walking through airports, my forehead sweating profusely.

Who cares? It’s all in the name of (questionable) fashion.

Heather in a cowboy hat on Halloween
This hat was worth it.

Terrible Tip #6: Forget Things Whenever Possible

When your trip has multiple stops, try to forget/lose at least one item — a plug adaptor, a sports bra, a beloved water bottle, maybe even a cell phone — in each place you go. Sometimes the item is lost forever. Other times you’ll need to nag a friend or family member to retrieve the forgotten item and mail it to your next destination, where it may or may not arrive in time. Luck of the draw — it’s exciting.

Terrible Tip #7: Ignore Good Travel Advice

Several American friends have recommended I apply for Global Entry status, which allows you to skip security and immigration lines at airports throughout the United States.

Ha! I scoff at good travel advice. Also I’m lazy. I’ll keep complaining instead.

Terrible Tip #8: Panic About All of the Above


* * * * * * * * * * *

That is all. I look forward to not learning from my mistakes and becoming an even more terrible traveler in the coming year.


  1. AutumnAshbough

    LMAO. I love that you own your “Wretched Traveler” status. And also that you got a cowboy hat. Any non-Canadian wearing anything besides a toque at any time is gutsy as hell and I bow before you.

    • 2summers

      Hahaha. I have already received quite a few strange looks and comments (I met my sister at the high school where she works and one of the students asked if I was acting in a play) but for some reason I don’t care at all. I love it.

  2. Catrina

    Haha! ???? Love that “advice”! Another one is to conveniently forget that you have packed laptop no. 2 in handbag no. 3 and let the security agent scan it several times until he finds it. Safe travels!

    • 2summers

      Hahahaha. Two laptops sounds like my worst nightmare 🙂

  3. Graham

    I see many like minded people trying to get the hand luggage into an overhead bin.
    It’s always good for a laugh.

    • 2summers

      Yes. And don’t even get me started on the exorbitant prices for checking bags that has led to an epidemic of people trying to squeeze their suitcases on as carry-ons. Which has hence driven some airlines to start charging for checked bags AND carry-on bags, which is extremely frustrating to me because I always have BOTH. I think I need to write a whole series of posts about my travel woes and complaints ????

  4. Louise Whitworth

    I hope you still have that hat! Hat purchased on holiday is exactly the thing I lose from having to wear it on the plane (like earrings, never wear those on the plane, lose them while sleeping every time….)

    • 2summers

      I’ve also made that lost-earrings-on-plane mistake. Haha. And yes I still have the hat for sure!

  5. John Sneed

    S0rry to have missed you and all your luggage on this trip. By all accounts it was fun.

    • 2summers

      It was so fun – you have to come next time. And by the way happy birthday John Doe!

  6. durbanroots

    My husband was pulled over as his case went through x-ray. We were all like, what’s wrong, as they uncovered his 7″ long serrated edged knife he’d randomly shoved in the case after we’d used it for the pears!!!

    • 2summers

      Ha! That must have been very sad and embarrassing????

  7. dizzylexa

    I love that hat, it really suits you.

  8. mvschulze

    You are a trooper. I did Kennedy to Tokyo years ago, nonstop, and going west it was like the sun would never set. Crowded std cabin, painful. Returning – empty Pan Am 747, fast asleep, landing and staying a week in Hawaii. Much better. M 🙂

    • 2summers

      Hahaha. I guess a week in Hawaii can cure anything.

  9. Lani

    This is great, and making me dread my trek back to the States next year. I’m just like you, I like to see new places, but I hate getting there and back. And it does get worse the older you get! Where were the days when it was fun and exciting???

    And my old cat used to sit on my suitcase, too. Awww, they are so cute.

    Not so funny story, I was in Denver Airport the day after they first opened/slashed moved to their new location which is in the middle of where tornadoes! land. Excellent planning, guys! And it was sooooo nuts. An overlooked detail was none of the phones would hang back up on their hooks, so staff had to keep trying and trying while the damn phones kept falling off.

    Glad you’re safe and sound back home! Cherish solid ground 😉

    • 2summers

      Hahaha. Glad you can relate. I HATED the Denver Airport.

      • Lani

        And a good way to deal with all of your adventures was to write about it – humorously. xxoo

    • 2summers

      Glad I’m not alone ????????

  10. David Pflieger

    Great article. Very funny. Just try to be courteous and mindful of others, especially the workers. Thanks for sharing!



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