Hey travel bestie,

This summer, we took a graduation trip for my son. It's kind of our thing to celebrate the big moments in iconic locations.

And my daughter couldn’t make it.

She had an internship. A really good one. The kind you don’t turn down. And rightfully so. I was proud of her.

But I’d be lying if I said it didn’t hurt a little, watching the three of us board a plane without her.

Here’s what I know, though: none of it would have happened at all if we hadn’t put it on the calendar first.

That’s the thing about family travel that nobody talks about. The planning isn’t just logistics. It’s a commitment. It’s saying, out loud, to everyone in the house: this trip matters, and we’re making it happen.

But life doesn’t always cooperate.

Teens have jobs. Young adults have internships. Work schedules don’t always line up. And sometimes, even the best-laid plans get rearranged.

That’s not failure. That’s just real life.

So here’s what I want you to take from this:

✅ Put the trip on the calendar anyway. Even if it’s tentative. Even if you’re not 100% sure everyone can make it. A date on the calendar is the difference between a trip that happens and a trip that lives forever in your “someday” folder.

✅ Pull school schedules, work schedules, and activity calendars at the same time. I know it feels like herding cats. But if you don’t look at everyone’s calendar at once, someone’s always going to have a conflict you didn’t see coming. Here’s how I think about fitting vacations into a busy family schedule​

✅ Plan with flexibility built in. A rigid itinerary is a recipe for stress. I always use Roadtrippers to map out our trips because it’s easy to move things around when plans shift.

✅ Have a backup plan and a backup date. If someone can’t make the original trip, talk about when you could do a smaller version or a different trip together. My daughter missed this one. But that just means we have a trip to plan with just the two of us. (Our backup dates just didn't work with my son's pending job offers)

Look, I get it. The window of time you have with your kids at home is shorter than it feels. I’ve said it before, and I’ll say it again — they’re going to move out sooner than you think.

And if you’re trying to figure out where to even start with summer planning, I’ve got you:

👉 24 Best Family Vacation Ideas with Teenagers

👉 How to Plan a Family Vacation

👉 How to Create a Travel Budget​

Put something on the calendar this week. Even a penciled-in weekend. It counts.

Tonya

Travel on!

Tonya

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