How to Be a Terrible Traveler: My Top 8 Tips

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.

“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.

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.

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.)

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.

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

Self-explanatory.

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