How to Write Humorous Travel Stories: Seven Ways to Ensure Something Goes Wrong On Every Trip

By freelance travel writer, Stan Sinberg

There’s a whole lot of travel writing I can’t, for the life of me, do:

I get bored silly writing long, adjective-laden descriptions of hotel rooms I’ve stayed in or of restaurants where I’ve eaten. Historical facts cloud my head, and I could barely tell you the difference between a moor and a monk. I wouldn’t know a high-thread count on a bed sheet if it bit me on the butt.

But I can make you laugh relating how I vastly overpaid for a Moroccan rug, traveled 5,000 miles to find a paramour, who, in retrospect, I should’ve been running from, and was almost driven to violence by a woman on my Galapagos Islands tour who was intent on keeping a running count of every turtle we saw.

In other words, my forte is misadventures. My misadventures. When it comes to humorous travel writing, my motto is: If Everything Goes Right, Something Is Wrong.

My favorite collection of travel stories are contained in a book called “Not so Funny When it Happened,” edited by Tim Cahill. Well-known writers like Bill Bryson, David Sedaris, Anne Lamott and many others share their tales of travel woe. One writer has his front teeth pulled from someone who turns out not to be the dentist; another writer almost drowns while her paramour doesn’t take a step to save her; and there are plenty of tales of encountering bewildering bureaucracies, vermin, and inedible food.

And they’re hilarious. Draw your own conclusions about what it says about the human condition, but the fact remains: hearing about the misfortunes of others often makes us laugh.

The very title, “Not So Funny When It Happened,” reveals the three essential elements that most humorous travel sagas contain:

1. Something went wrong.
2. It wasn’t funny at the time.
3. It is now.

Let’s take them one at a time:

Something went wrong. Think of your funny (and best) travel stories. I bet most of them involve a misadventure, a missed connection, a misunderstanding, a horribly misbegotten hotel or restaurant, or perhaps even a miserable romance. In short, disaster (or something feeling like it) struck.

It wasn’t funny at the time. No. Of course it wasn’t. You were wet, tired, scared, anxious, angry, cold, hot, sick, uncomfortable, exasperated, infested, rejected, ripped-off, confused, depressed, debilitated, lonely, sad.

It is now. Time has passed. You’re OK. No one was mortally wounded, lost a limb, or was otherwise permanently damaged. In other words, the consequences weren’t dire. You may have lost time or money or bodily fluids or suffered a broken heart, but now you’re safe and sound, and you can laugh about it. And more importantly, as a travel writer, you can make others laugh about it, too.

“Gee,” you’re saying at this point, “I’d love to write a story like that, too, but nothing like that ever happens to me.”

Well, I’m going to make a suggestion that may sound off-the-wall, but which I can pretty much guarantee you will help. And that is: Take it upon yourself to get into trouble.

What do I mean by that?

I’ve been on press junkets where we stayed in five-star hotels, were chauffeured around in mini-vans and buses to top restaurants with all-star chefs, followed by tightly run city tours with stops for shopping in well-known tourist meccas, and I can safely say, almost without exception, that these experiences yielded almost no material for me. But when I drifted off on my own, when I escaped the tour to go wander solo among the Great Unwashed, I had to beat story ideas off with a stick.

Because when I cede control, that’s when things start to go wrong, or at least awry.

Am I suggesting that you put yourself in danger? Of course not. While journalists may want to kill for a story, it’s not a good idea to die for one. But you can still increase the odds that something amiss will occur — and make good copy — by doing some of the following:

• Arrive in town without a hotel reservation. Instead of getting off a plane and being immediately whisked away in a van to your pre-booked hotel, arrive without one. It’ll force you to interact with the assorted taxi drivers, rooming-house operators and other characters who typically wait around airports. Talk to them. Go with one. Let them recommend a hotel. Or get dropped off in town. Wandering around town with your bags looking for a place will virtually assure lots of contact with locals who want to “help” you.
• Stay in two-star — or less — hotels. The comfort and amenities will be minimal, for sure, but you’ll get exposed to the local culture.
• Get away from the tour group. As mentioned earlier, leave the group whenever possible. Go off on your own. Eat in an unfamiliar restaurant, walk in a strange neighborhood.
• Get lost. On purpose. Don’t take a map. Just wander. If you start to wander where you don’t feel safe, retrace your steps, ask a cop, or make a call on your cell phone.
• Stay an extra few days. If you’re on a package tour, see if you can extend your stay a few days and go back to places that interested you, or new ones, by yourself.
• Interact with the natives. When strangers approach, asking us for money or offering to “help,” our instinct is to say “No,” and continue walking. Instead, leave most of your valuables in your hotel, and let yourself be engaged. That way, if you do get swindled, your loss will be minimal. You’ll probably recoup it making it into a good travel story.
• Have a “fish out of water” experience. River-raft. Kayak. Go dog-sledding on a glacier. Hopefully nothing will go wrong. But the very act of trying something foreign when you’re way out of your element, will likely yield amusing results.

And you know what else? A lot of time, nothing much will go wrong. You’ll find the hustlers charming, and the hole-in-the-wall hotels and the restaurant you’ve never heard of to be perfectly suitable. If things go smoothly, at the very least you’ll feel like you had a more “native” experience And should some misfortune happen that makes you uneasy, hungry, wet, poorer, or feeling stupid — well, chances are you just got yourself a story. And a funny one, at that. You just may not know it at the time.

[Editor’s Note: Learn more about opportunities to profit from your travels (and even from your own home) in our free online newsletter The Right Way to Travel.]