travel

Marco's Guide to Booking Flights Wrong

April 1, 2026

I booked the cheapest flight available. It departed at 4am. I did not sleep. I did buy twelve-dollar airport socks.

So you want to travel. Great. Terrible idea. But since you're doing it anyway, let me save you some time by explaining exactly what I did — so you can do the opposite.

Step One: Book the Cheapest Flight

It departs at 4am. That's fine. You'll sleep on the plane.

Spoiler: you will not sleep on the plane. You will watch three episodes of a show you don't even like, eat a small packet of pretzels with the intensity of someone who hasn't eaten in days, and arrive at your destination looking like you lost a fight with a time zone.

The 4am departure sounds efficient. It is not efficient. It is just 4am.

Step Two: One Carry-On Only

You're being efficient. You're being smart. You pack for five days in a bag the size of a large sandwich. You are very pleased with yourself.

You forget socks. Not one sock — all of them. Every single sock failed to make the bag. You are now standing in an airport at 6am buying socks for twelve dollars each from a terminal shop that is absolutely aware it has a captive audience.

I bought three pairs. I now own those socks. They are my most expensive socks.

Step Three: Skip Travel Insurance

Nothing will go wrong. Nothing ever goes wrong.

Everything went wrong. My flight got cancelled, rerouted through a city I genuinely cannot pronounce, and I arrived two days late to a hotel that had given away my room to someone who, presumably, arrived on time and with socks.

But I saved forty dollars on insurance, so technically I made a profit. That's how finance works, I think.

Step Four: Don't Plan Anything — Just Vibe

The vibe will be confusion. The vibe will be standing outside a restaurant for forty-five minutes because you didn't book and now it's full and every place nearby is also full and you end up eating a gas station sandwich at 9pm in a foreign city wondering where it all went wrong.

It went wrong at "just vibe."

What Actually Worked

Here's the thing — and I mean this genuinely — travel is incredible even when it goes sideways. Especially when it goes sideways. The best story from any trip is never "and then everything went exactly as planned."

The sock situation became a conversation. The cancelled flight gave me six unexpected hours in an airport where I had the best coffee I've ever had and finished a book I'd been meaning to read for a year.

Plan enough to have a direction. Leave room for the rest to be a story.

Just bring the socks.