The passerby spotted Henry and me sitting, hot and furious, like a pair of livid living bookends on a public bench in San Francisco. Given he was five, my son had the better excuse for acting like a sleep-deprived toddler, but both of us were in enraged two-year-old mode.

“Hi!” the stranger said cheerfully, approaching with an even mix of hope and caution.
Henry and I shot her a collective wary look.

“Hey!” she continued, “There’s a parade down the street! Free food, too! You should go! You’ll have fun!”

Here’s what I can observe now, from a distance of 20 years and 20,000 paces: I should have let him get the stupid action figure.

I mustered an ounce of faux-cheerfulness and thanked her. I really did appreciate her efforts to diffuse what she could clearly see was a meltdown mother-and-child moment. But Henry and I were way too irritated to take her advice.

Our fight’s catalyst was quite ridiculous. Henry was exhausted after a day of tromping up and down the hilly streets through Chinatown and North Beach. We wandered into a tourist trap tchotchke shop and I told him he could select one souvenir. He spotted an action figure he wanted to add to an already abundant collection back home. I decided a toy cable car would be a more fitting memento and urged him to get that instead. Thus began our little war.

Ask me if I can remember which item he wound up getting. Of course I can’t. But I will never forget just how determined we each were to have it our own way— enough that a total stranger could observe our fury from twenty paces.

Henry and Spike in Brooklyn in later years

Here’s what I can observe now, from a distance of twenty years and twenty thousand paces: I should have let him get the stupid action figure. Because I did tell him he could pick something out, and then, in my attempts to persuade him otherwise, I ruined an otherwise lovely day.

I firmly believe that to successfully travel with little kids, it’s crucial to give them choices. Real choices. In a moment of exhaustion, panic, or the belief that as the adult you can make “better” trip decisions, it’s super easy to slide into alpha mode. This, in turn, most often prompts a defiant response—no one likes being bossed around—and voila: unnecessary, vacation-ruining fight.

Our best travel memories hinge on times Henry had some say in the itinerary. This offered him the comfort of feeling some control in unfamiliar places, and me the thrill of seeing things I might not have otherwise appreciated. Like the time he was four and wanted to run up and down every dirty, disgusting mound of old snow we encountered on a trip north. Once I let go of my inclination to stop him, I took in the joy on his face and felt it myself. Unlike me, my son did not grow up in a place with snow—he didn’t care that these mounds weren’t pristine and white. IT WAS SNOW!!!

To successfully travel with little kids, it’s crucial to give them choices. Real choices.

Active listening and keen interpretation skills are the best tools you can bring when traveling with kids. On a trip to New York , again when Henry was very little, he had another moment of frustration, which he expressed by hollering, “TAKE ME BACK TO AUSTIN, TEXAS RIGHT NOW!!” in the middle of the Metropolitan Museum of Art.

I understand now that what he really meant was he felt very unmoored after yet another of my over-compensatory whirlwind itineraries. As a child I had never traveled out of the state in which I was born. I was determined that my son would see as much as I could show him in the world, which sometimes pushed him past his limits. Forget about looking at masterworks. He just wanted to be home in his own bedroom. (In fact, one time he shouted his TAKE ME BACK TO AUSTIN when we were actually in Austin, which is when I figured out “Austin” translated to “a place where I feel safe and familiar.”)

I imagined myself in his little shoes
and understood his request clearly.

And then there was the time we toured Pacific Coast Highway. After many nights staying in antique-packed B & B’s and eating in extravagant restaurants, all the kid wanted was a Best Western and a grilled cheese sandwich. That time I heard him loud and clear. I did not feel put out by his insistence on doing things his way. Instead I imagined myself in his little shoes and understood his request clearly.

He was happy I honored his wish. I was happy he was happy. And so, content together, we found that chain motel and generic grilled cheese easily as wonderful as the fancy-schmancy joints we’d visited earlier in the week. He delighted in the familiar comfort of melty American cheese and I delighted in the reminder that to truly travel together it was vital that I honor his desires, too.

Spike Gillespie is a single mom, daily meditator, compulsive knitter, and the critically acclaimed author of eight books and countless magazine articles. Her work has appeared in The New York Times Magazine, The New York Times, The Washington Post, Real Simple, GQ, Esquire, Elle, Smithsonian, National Geographic Traveler, Interweave KNITS, The Christian Science Monitor, Texas Monthly, The Dallas Morning News, and other publications. In 2006, Austin Chronicle readers voted Spike the Best Author in Austin.