I’m sure I’m not alone in sometimes being too cheap for checked luggage when traveling for short fly and ride adventures… or am I? Either way, here are some of my most memorable airport security misadventures shared here for entertainment and educational purposes.

The Mosko Moto Jason Bourne Tactics vs WD40

Time stood still as I approached airport security in Malaga, scanning the two lines closest to me. Strategy was everything; the world hung in precarious balance. One wrong move, and I’d spend an unbearable seven to eight, potentially NINE minutes at security instead of the more acceptable four or five.

For a split second, I felt like Jason Bourne analyzing escape routes. Would I risk the line with two elderly gentlemen and a young girl, or aim for the large family (all five members already moving) and a guy wearing a hat with the most fabulous feather?

Now, I’m usually not this petty. Or rather, I’m averagely petty when it comes to airport security; sometimes I just accept defeat in advance, put an audiobook on, and take it easy. But I was headed to Mexico and I needed a win today, even if it came in the form of nailing the security line choice.

The Tactical Analysis: Line A: Two old timers (one deeply puzzled by his own belt buckle, one seemingly unaware he was at an airport at all) and a young woman lost in TikTok land. Line B: a family of Clan MacVeryLoud (but efficient, moving quickly) and Feather Hat Dude (displaying Austrian-level precision with his electronics).

I chose Line B.

Success! The last MacVeryLoud had cleared the scanner, and Feather Hat was methodically organizing his belongings like a TSA Marie Kondo. This was going to be a three-minute victory—four, tops. Feeling magnanimous in my tactical efficiency, I even complimented Feather Hat on his headgear.

I sailed through the scanner like a graceful gazelle, Gate D48 tantalizingly close, my airport security strategy clearly superior to mere mortals…

And there the story would have ended, if it wasn’t for one tiny detail:

I wasn’t, as it turned out, a Graceful Airport Security Gazelle, but rather The Moron Who Forgot About the Can of WD40 Rolling Around the Bottom of My Mosko Duffel.

As I watched a frazzled security agent unpack my carefully organized gear while both elderly gentlemen from Line A were probably enjoying their espressos and Clan McLoud were likely already boarding their plane, I realized that perhaps my airport security chess skills needed some work. Or maybe I just need to stop storing random maintenance supplies in random bag pockets.

The Portuguese Eau de Cow

Ever wondered what happens when rally training meets agricultural reality? Well…there was that time I decided to be smart and fly to Portugal wearing all my gear for a three-day rally bootcamp. The flight there? Smooth sailing. The training? Fantastic. The flight back? Well…

Here’s a pro tip: when crossing farm fields during training, perhaps consider that those innocent-looking puddles might not be filled with spring water. But there I was, splashing through what I initially thought was just rain runoff, until that distinctive agricultural aroma hit me.

By the time I got to the airport, my Klim gear had developed its own unique fragrance – a special blend of “Essence of Cattle” with subtle notes of “Why Did I Do This?” I’ve never seen a more strategic deployment of social distancing than my fellow passengers quietly relocating to different rows.

To the entire crew and all passengers of that flight: I am deeply, profoundly sorry. I know you probably still tell stories about that one rider who brought the entire farm into the cabin. In my defense, I did try to become one with my seat, hoping it would somehow swallow me whole. It did not.

Coffee à la Helmet

Here is my philosophy about carrying helmets: They ALWAYS go in the cabin with me. Always. This steadfast rule has served me well, except for that one time over Central America when I learned that “regional flight” is code for “sardine can with wings.”

Picture this: no overhead bin space, three hours of flight time, and a helmet perched precariously on my knees like some sort of awkward coffee table. Speaking of coffee: Did you know that turbulence and hot beverages are natural enemies? I do now.

One unexpected bump, and suddenly my helmet liner became intimately acquainted with my morning americano. With no time to wash it before the ride, I spent the next few days experiencing what I can only describe as “helmet coffee shop syndrome.” All the coffee smell, none of the caffeine benefits.

The silver lining? At least it wasn’t farm puddle water.

So there you have it: From WD40 contraband to coffee-flavored helmet liners and bringing an entire Portuguese farm into economy class. If there’s one thing I’ve learned, it’s that adventure begins way before you hit the trails.

But surely I’m not the only one with tales of airport security theater and carry-on gear chaos? Share your own fly and ride wisdom in the comments below. How do you handle gear at security? What’s your strategy for not being That Person on the plane? Any creative solutions for keeping your helmet from becoming an overpriced beverage holder?