
Before we had even taken off from the New Orleans airport, our son declared, “After this, I don’t want to take another trip for a while.”
Someone once said that the definition of insanity is doing the same thing over and over but expecting different results. That person may have been witness to our undying optimism that we will eventually travel well together as a family.
Some families enjoy a deep love for traveling together. That must be so nice for them.
You’d think that with only three of us, we’d be able to pull off a happy travel experience. But…you’d be wrong. We are actually three of the most opinionated, picky people on the planet (who expertly dispense humor in an attempt to offset how frustrating we can each be).
So why do we keep trying?
When Family Vacations Go Wrong Before They Even Start
Several things always go wrong. It’s basically built into the process. Late Uber rides, missed flights, lost bags, incorrect forms of identification, room keys that suddenly quit working, random work emergencies, an AC unit that stops blowing cold.
On this trip, the first one was mine. For days leading up to the trip, I reminded my husband that he’d have to travel with his passport, since he only has his digital wallet at the moment (his wallet was stolen when his truck was broken into on another trip, which tells you everything you need to know about how we travel). I was feeling good and self-righteous about catching this issue before it became a problem. Out of an abundance of caution, I threw in my passport as well, because why not.
Who Checks the Expiration Date, Anyway?
When we got to the airport, for reasons that truly make no sense to anyone, including me, I decided to leave my physical license in the car and use my passport too.
At TSA Pre-Check, Chad and Sam got through without issue. I was informed that my passport was expired (and therefore invalid as identification for travel). The short of it is, about 15 minutes of paperwork and $45 later, my son could quit sending me, “OMG Mom, are you getting arrested??” texts.
Dr. Daniel Amen says when he and his wife travel, they have a game where they don’t get frustrated until 12 things go wrong. What a great goal. We can make it to about 1.5 things before we lose our cool. Distress tolerance building blocks, I say!

His airport declaration was followed by four days of questions like, “When can we go back to the hotel?” And “What are we doing after this?” And “Will we be together the whole time?”
That boy is a tried and true homebody. He loves anticipating a trip, and once we get there, he looks forward to being home. At one point he announced, “When we get home, I’m going to have big chill time and grind on my games with my friends.” He’s happy to be anywhere his favorite people are, but when he’s done, he’s done. (My husband, on the other hand, is happy as a clam in any new moment he finds himself. So therein lies the problem.)
Stuck Together (Literally)
At some point on a trip, we like to get into a family fight. It’s usually after no one read my mind and deciphered the one thing I really wanted to do but did not communicate to anyone so I’m feeling particularly primed for martyrdom. Or it’s because no one wants to hear my life lessons, and apparently everyone is allowed to have their own moods and not love every single thing I planned.
We usually make up over food.
The one thing we do really well as a family is find delicious food.
On this trip we scheduled an Italian food tour in Boston’s historic North End. As we sat in the basement of an old Italian restaurant, I expected to have another fantastic Italian dish and a nice glass of wine. We had already experienced several unbelievable bites and learned a lot about the area. (And surprisingly, all three of us were really into it.)

What I didn’t expect was a side of life wisdom to go with our Sangiovese! Our tour guide, Paula, made an off-handed comment about how “Wines are like people: you can tell when you meet someone and they’ve never been through anything hard. They’re just not that interesting or fun to be around.”
As a pastor’s daughter, I have a sixth sense for what can be turned into a sermon illustration, so I caught it right away. She went on to describe how vine growers will intentionally hold back water so the roots go deeper into the soil looking for it. The result is a grape that is much more robust and flavorful.
By that standard, our family is fascinating.
Shared misery is bonding.
This trip’s low point was when our flight home was cancelled after we had checked out of our hotel and were more than ready to be home. We had to figure out what to do to kill six hours in Boston while it was cold and drizzling all day.
The Great Boston Tea Room Standoff
We ended up in the tea room of the Boston Tea Party Ships and Museum, where Chad suggested we find another museum to go to. Sam and I, perhaps empowered by the story of the Tea Party, staged our own revolt. Sam made our case: “We have done everything you have asked. We have seen all the things, gone to all the places, walked a million steps. And now Mom and I are done. You can go to another museum, and we will hang out in the hotel lobby.”
Then we all just sipped our tea in a standoff.
In the silence, I shouted, “If I hear ONE MORE PATRIOTIC SONG, I’m going to grab that fife and shove it where the sun doesn’t shine.”
All three of us died laughing in a fit of delirium.
You have to really be at your wit’s end to engage in that level of humor, and that is where we were. Somehow, that line will go down in family lore for generations to come.
Then we rallied and agreed to “one more thing” to kill some time.
The Trip You Plan vs. the Trip You Remember
The stories we retell around the dinner table are always the ones where everything went sideways: the expired passport, the standoff over tea, and of course, the fife.
In our regular suburban life, we don’t face too many vine stressing moments. (Once, Sam said the hardest thing he had ever been through was an infected bug bite, bless his heart. He conveniently forgets about that time our house had six feet of water in it.)
I’m not saying we’ve never been through anything hard (that couldn’t be further from the truth), but our day to day life is pretty ordinary and basic, filled with school, work, soccer practice, church, and TV shows. Travel shakes us out of all that. It makes us a little crazy, and it gives us something to laugh about for years. I’ll take that over a picture perfect trip any day.
To every family that travels anything like ours: I hope your next trip goes a little more smoothly. And if it doesn’t, I hope you find something to laugh about anyway.
For your own picture perfect trip, I wrote a free family vacation ebook called The DIY Family Retreat to help you find a few minutes of real connection, even if it’s at baggage claim waiting on a suitcase that never shows up.

