Bill surprised me with a trip to Dave & Tim Riviera Maya in Mexico after we had only been on six dates—a bold move that turned into one of our most unforgettable adventures. Between floating in the pool with margaritas, discovering incredible artists like Mt. Joy, and dancing barefoot on the beach to Dave Matthews and Tim Reynolds, the trip had the kind of magic only music, sunshine, and great people can create. It was more than a vacation—it was the moment I realized this spontaneous trip (and maybe this relationship) was going to be something special.

We traded beach trips for a winter adventure in Banff—and gained something far more meaningful than a vacation. From deep conversations over dinner to unforgettable experiences in the Rockies, this senior-year trip highlights why one-on-one travel is one of the most powerful graduation gifts you can give.

When my kids entered high school, I made them a promise: every year they’re in high school, I will take them on one one-on-one trip anywhere in the world they want to go.

No siblings. No compromises. Just the two of us.

At the time, I didn’t fully realize how transformational that promise would become — not just for them, but for me.

We had less than a month to pack and prep, which is always a little chaotic. But the real curveball came the day before we left: the government shut down. Airports across the country were short-staffed as TSA employees weren’t being paid. For us, that meant three cancelled flights before we finally boarded a plane from Philadelphia to Miami—after a three-hour delay.

Traveling abroad is exciting—new cultures, new sights, new experiences. But if you’re traveling with a picky eater, the excitement can quickly turn into anxiety. Meals become negotiations, menus feel intimidating, and you may worry whether your child (or partner!) will eat at all.

The good news? You can travel internationally with picky eaters and still have a positive, meaningful trip. It just takes a bit of planning, flexibility, and reframing expectations.