My parents never took me overseas. I always said I’d do it with my kids. Fiji was the first attempt. Charlie cried on the plane. Thomas cried at the resort. Both cried at dinner while other guests tried not to stare. By the second morning, I was wondering if I’d made a terrible mistake.
It took three years to try again. In Bali, Charlie screamed for hours on the first night, eventually falling asleep on the floor next to the front door. I felt like doing the same. Nothing had improved.
South Africa was the first trip where nobody cried
When the boys were 9, I had a work conference in Cape Town. My wife, Cece, flew 14 hours alone with them to meet me. Charlie arrived jetlagged and emotional, refusing to eat.
But before we headed out on safari, I arranged a visit to an orphanage. The boys brought an Australian football and spent the afternoon teaching the kids how to kick it. I watched them run around for an hour, completely ignoring me. Nobody cried. Or refused to eat. It was the first trip where I stopped apologizing to people.
The crying stopped, the obliviousness didn’t
I’d plan every detail of a trip, and the first question each morning was “Where are we going today?” If I asked what they wanted to do, the answer was a shrug or “whatever.” I’d ask if they’d packed, and they’d say yes. I’d check and find no toothbrush.
Thomas had toiletries confiscated at security so many times that I stopped replacing them. AirPods went in at the gate and didn’t come out until we landed. Between stops, both sat in the back seat staring at their phones while entire countries passed the window.
When they were 16, we visited Washington DC and spent time at the Holocaust Museum and the National Museum of African American History. I expected the usual half-glances at plaques. Instead, they stopped. They wanted to talk about what they were seeing.
A year later in Sri Lanka, a cooking class ran long because the boys spent half of it swapping travel stories with backpackers, talking about places we’d visited. Afterward, unprompted, both said they were glad we’d booked it. Not my usual feedback. But I still checked their rooms for forgotten chargers.
Mexico was the first time I’d ever had a drink with my own kids on a trip
When the boys turned 18, we took a trip to Puerto Vallarta. One afternoon, we wandered into a small tequila bar for a tasting. We sat at the counter and worked through the pours while the bartender explained each one.
What I didn’t know was that after we left, they went back. They found the man behind the counter and asked which one their dad had liked. He pointed them to a bottle of Don Cayo. It’s a small local brand you can’t find outside Mexico.
A few weeks later, it was under the Christmas tree. It’s the best present I’ve ever received.
For 18 years, I was the one who remembered everything
I booked the flights, checked the bags, replaced the confiscated toothpaste, and tried to make it fun. Past presents from the boys were usually a book I’d suggested that my wife had to buy. Sometimes they didn’t even manage that.
The Don Cayo wasn’t a book I’d chosen. Nobody told them to go back to that bar. These are the same kids who couldn’t remember to pack deodorant. But they remembered which tequila their dad liked.
I keep it for special occasions. It almost makes me forget the Fiji fiasco. Almost.
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