As the holidays roll in, here’s the one family travel truth I’ve learned after 13 years on the road:
Expect chaos.
That’s it. That’s the trick.
Family trips aren’t meant to be flawless. The highs are magical — but the lows? They’re inevitable. Flights get delayed. Kids melt down at 2 a.m. The weather turns. Someone finds a hair in their food. Travel isn’t an escape from real life — it is real life, just in a different zip code.
And once you accept that? Everything feels lighter.
The Magic + the Mess
Last weekend, my kids and I drove to Connecticut to see old friends. We ate chicken sandwiches, played ping pong, floated in the pool, watched Alexander and the Terrible, Horrible, No Good, Very Bad Day, and drank cold white wine from tiny Italian glasses. I kept thinking, This is what it’s all about.
At the same time:
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The boys argued nonstop in the car
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I snapped (misophonia is real)
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Our Airbnb had huge bathroom spiders
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We lost a basketball in thorny bushes
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The drive home was pure traffic misery
Annoying and wonderful. Both true.
Family Travel, in One Sentence
A friend once summed up a trip like this:
“It was bad, and then it was great.”
Honestly? That’s the genre.
You’ll yawn through famous sights. Get hangry in beautiful places. Feel too hot, too tired, too done. And then — five minutes later — you’ll have a moment you’ll remember forever.
That’s the deal. That’s the beauty.
If you go into family travel expecting perfection, you’ll be disappointed.
If you go in expecting both the mess and the magic, you’ll probably have a great time.
What about you — what’s the funniest, worst thing that’s happened on a family trip? And have you ever had one that truly sucked? (It happens.) We’re aiming for wholeness, not highlight reels.
