The #1 Trick to Enjoying Family Travel: Expect the Rough Patches! (2026)

Ready to unlock the secret to actually enjoying family travel? After over a decade of navigating family adventures, I've discovered the single most crucial key: Expect the unexpected, and embrace the chaos!

We're heading into the holiday season, and it's the perfect time to revisit this gem about family travel. Toby also shared some fantastic tips for surviving family trips, and I've got my own personal trick for making those big family gatherings a little more bearable. Good luck out there, and here's to making memories!

After 13 years of traveling with my family, I've finally put my finger on the magic formula for fun (or, at least, how to articulate it): anticipate the rough patches.

Travel is all about those soaring highs, right? But, especially when you're traveling with family, the lows can be, well, hilariously low. A few things are practically guaranteed: flight delays, headaches, rainy weather, kids waking up at the crack of dawn, or even finding a rogue hair in your salad. And honestly, isn't that just part of the deal? Travel is still real life, and those tricky moments aren't disasters; they're just... life.

Take, for instance, a recent weekend trip with my boys to visit old friends in Connecticut. We feasted on chicken sandwiches, played ping pong, and floated in the pool. We watched "Alexander and the Terrible, Horrible, No Good, Very Bad Day" and sipped cold white wine from those cute little Italian glasses. There were countless moments when I thought, "This is what life is all about."

But, let's be real, it wasn't all sunshine and rainbows. The boys bickered during the three-hour drive. I got a case of misophonia and had to threaten to turn the car around. Our Airbnb had some rather large spiders in the bathroom. We lost our basketball in some thorny bushes. And the drive home? Total gridlock.

The takeaway? Parts of the trip were annoying, and parts were epic. Both can be true!

Here are some travel snapshots from years past:

  • Yawning through the glorious Laguna Gloria in Austin.
  • Getting a "Plus Four" card during an Uno game in San Diego.
  • Not feeling the beach in San Francisco.
  • Tired of walking in Italy.
  • Hangry in England.
  • Too hot in Florida.
  • Heading onto a 10-hour flight.

My friend Andy recently summed up family travel perfectly with a single sentence: "It was bad and then it was great." Isn't that the truth?

And let's not forget two legendary posts that always crack me up:

  • Vacation or Trip? A Helpful Guide for Parents
  • Mom Spends Beach Vacation Assuming All Household Duties In Closer Proximity To Ocean

But here's where it gets controversial... Do you agree that the bad moments are just as important as the good ones? What hilariously awful things have happened to you on family trips? Have you ever had a trip that was just a total disaster? Share your stories below—we're all aiming for wholeness, after all!

P.S. Here's an ode to bad family vacations, and the weirdest, best part of trips.

The #1 Trick to Enjoying Family Travel: Expect the Rough Patches! (2026)

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