Anniversary Trip Interrupted: How O’ahu Proved We Could Travel the World with Kids
The Trip That Changed Everything
In 2010, Bryan and I hit our 10-year wedding anniversary and decided we were due for a romantic getaway. I was picturing gondola rides in Venice, sipping Chianti in Tuscany, and maybe even reenacting a few scenes from Under the Tuscan Sun.
Then reality tapped me on the shoulder - loudly.
We had three kids: ages five, four, and one. The only thing we’d be “sipping” was apply juice from a sippy cup. Suddenly, those dreams of Italian romance looked a little more like Under the Capri Sun.
The Dream Meets the Diaper Bag
We still wanted something special for our anniversary, but babysitting for a week? Out of the question. Somewhere between diaper changes and lost pacifiers, we realized we didn’t have to put our travel dreams on hold until the kids were grown. So we changed the question entirely: How can we travel somewhere amazing—together—as a family?
The checklist was ambitious:
Kid-friendly outdoor adventures
Quick dining options for hangry meltdowns
Stroller-friendly hiking trails
A budget that wouldn’t make us cry
A resort nice enough that “lazy day” felt like a vacation, not a punishment
And, of course, a place where Bryan and I could maybe (just maybe) sneak in a few quiet moments and sips of something other than milk.
It sounded impossible. Until Hawaii kept popping up on my late-night Google searches.
Why O’ahu? The Perfect First Island for Families
Each island had its charm—the Big Island with its fiery volcanoes, Maui with it’s winding Road to Hana, and Kauai with its wild, untouched beauty. But after 10 hours on a plane with three kids, we weren’t about to sign up for another flight just to island-hop.
So, O’ahu it was.
And honestly? It was perfect.
In 10 blissful days, we soaked up beaches, waterfalls, luaus, and laughter. There were early mornings, sticky shave-ice hands, and a lot of sunscreen reapplications. We never ran out of things to do—only energy to do them all.
By the end, we even had a “next time” list that was twice as long as our original plan.
The Big Aha Moment: We Can Travel Anywhere With Kids
Somewhere between chasing toddlers through tide pools and watching the sun dip below Waikiki, it hit us: we could travel anywhere with our kids. Italy, France, New Zealand—you name it. It was all possible - with a little planning, a lot of flexibility, and a sense of humor.
The secret? Turns our it wasn’t finding the “perfect” family destination - it was in balancing cultural and kid-friendly experiences, fine dining and “eat with your hands” meals, planned activities and spontaneous detours. And above all, the ability to pivot when naps, moods, or weather didn’t cooperate.
I also learned a golden parenting truth: never interrupt genuine joy for a photo. If you shout “Smile!” mid-sandcastle, the joy (and the sand) will vanish instantly.
What O’ahu Taught Us About Traveling as a Family
That trip didn’t just give us an anniversary to remember—it reshaped how we travel.
We realized adventure doesn’t have to pause when you have kids; it just gets louder, stickier, and a lot funnier. O’ahu showed us that the world is wide open—whether you’re sipping Chianti in Tuscany or juice boxes by the pool.
And from then on, we knew: we could travel anywhere, with anyone, at any age. Goldfish crackers and all.
Family Travel Takeaway
Don’t wait for the “perfect time” to travel with your kids. There’s no such thing. But there is a perfect opportunity—to make memories, embrace chaos, and see the world through their wide-eyed wonder.
