February 22, 2025 4:34 am EST
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  • I make sure to plan regular individual trips with each of my two kids.
  • It’s often when we have our most honest conversations.
  • It’s also nice to be focused on just one kid at once without any distractions.

Just 18 summers and 18 spring breaks — that’s really all you get when it comes to vacations with the littles (and honestly, those first few don’t really count). When you think about it this way, you start to understand how important and precious downtime with them is. Not that they won’t want to hang with you when they’re in college and launched. But honestly, you can’t bet on it.

Even more rare is getting honest-to-goodness alone time with each kid. No siblings, no spouse. That’s when so much of the good stuff happens. Here’s why going on one-on-one trips with each of my kids is such an important part of our family vacation strategy.

You get the straight talk

By removing all the distractions of friends and the rest of the family, you get the rare opportunity to have real-talk with one of your favorite people on earth. This gets more and more important as the kids get older and they share less and less with you in the course of normal life.

On my one-on-one trips with my kids, we’ve broached every subject — from romantic relationships to visions of the future they want for themselves to real feelings about drama with friends. It’s calm, safe, and connected.

You can be laser-focused on just one kid

I have two kids, but most of the time, my husband and I think about them as one monolithic unit — “the kids” — rather than as individuals. Going away with just one of them means they get your complete focus.

Without distraction from siblings or even the other parent, you get to reconnect with them as unique people. You’ll learn more about them as an individual, as well as your relationship with them.

No one else’s point of view compromises their own

Although I think both my kids are spectacular, one tends to railroad the other, more accommodating kid (and I mean this in a loving way). Taking them away to spend individual time with me means they each have time to truly express their own unfiltered, uninfluenced opinion.

No one is worried that their choice of activity isn’t cool enough for the other sibling or that Dad will be bored. It’s a rare chance for each kid to feel like an important “only,” and it makes them feel super special.

Your kids get to choose what to do, and it doesn’t have to be a big expensive trip

It’s not about whisking your kid away for a week on a beach — although that’s fun, too. We’ve done as many one-on-one days as we have overnights. There was the time I won Harry Potter tickets in the Broadway ticket lottery: I sprung my youngest from school for the day, and we had an amazing adventure, sitting front row at the show and eating at the super touristy Cain’s Chicken around the corner for lunch.

This is, of course, the last place on earth I would eat if my husband and I were making the dining picks, but that’s the point: my then-14-year-old son got to make all the decisions of the day.

Absence makes the heart grow fonder

Frankly, when you’re away with one member of your family, you miss the others, and they miss you. That makes coming home almost as lovely as the vacation itself and makes the other kid excited to plan and take their own special trip next. Win-win.



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