Traveling with teenagers isn’t just different from traveling with little kids — it’s an entirely different season of family life. Our daughter Callan is now 21, our son Jake is 19, and Max is 16, and somewhere along the way we realized that the trips that worked beautifully when they were younger no longer fit who they are now.

They want independence, adrenaline, food that feels intentional, and experiences that don’t feel designed for kids. They want late nights — but not forced ones. Energy — but with an exit plan. And when it comes to New Year’s Eve, they want it to feel like a real celebration, not something they’re tagging along to.

Over the years, five destinations have consistently risen to the top for us. Not because they’re flashy, but because they allow New Year’s Eve — and the days around it — to unfold naturally with teenagers and young adults.

Let’s be honest: sustainable travel sounds lovely in theory — but when you’re juggling three kids under six, it can feel about as realistic as meditating on the plane. (Spoiler: I tried. It lasted two minutes, right until someone’s bag of pretzels went flying.)

But here’s the truth — traveling more sustainably with little ones is possible, and surprisingly, it actually made our trip to Oʻahu calmer, richer, and more connected. Here’s how we did it — what worked, what didn’t, and how the kids accidentally became tiny eco-warriors along the way.

So, you’ve decided to take your family to Hawaii — cue the ukulele music and the logistics headache. Which island should you pick? Each has beaches, palm trees, and shave ice, but when you’re traveling with three kids, not all tropical paradises are created equal.

We did the research (and lived to tell the tale). Here’s your crash course on the Big Four — Big Island, Maui, Kauaʻi, and Oʻahu — and why our crew of five ultimately landed on Oʻahu.

I thought I was taking my kids to Pearl Harbor to teach them history. Turns out, they were teaching me.

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.

There are vacations… and then there’s Oahu. The moment we stepped off the plane and were “lei’d” upon arrival (yes, we giggled too), we knew we’d landed somewhere special. Between the soft trade winds, turquoise water, and the faint smell of sunscreen and pineapple in the air, it’s impossible not to slip instantly into island mode.