Aloha Reader!

Did you see the viral story about the grandma who took eight grandchildren to Hawaii? The photos had me tearing up at my computer, and apparently I wasn't alone – it's been shared millions of times with comments like "This is what family looks like" and "Goals for when I'm a grandparent."

But here's what caught my attention as a Hawaii travel expert: this isn't just a cute story. It's part of a massive shift in family travel that's creating some of the most meaningful vacation experiences I've ever seen.

It's called "skip-generation travel" – where grandparents take grandkids on vacation while parents stay home and actually get a break.

The numbers are wild:
→ 79% of grandparents now plan skip-gen trips (up from basically zero five years ago)
→ 89% of millennial/Gen-Z parents want more quality family togetherness
→ 72% would even pull kids from school for meaningful family experiences

And Hawaii is the #1 destination for these adventures.

Why skip-gen Hawaii trips work so well:

For Grandparents: You get to be the adventure leader, not the babysitter. You're creating memories and sharing experiences without parents as intermediaries.

For Grandchildren: Undivided attention from grandparents, plus they often step up and become more responsible and confident travelers.

For Parents: You get a REAL break while knowing your kids are having the experience of a lifetime with people who love them unconditionally.

The magic I keep hearing about:

Grandparents are coming home saying things like "I never knew my granddaughter was so brave" after snorkeling adventures in Maui.

Kids are writing thank-you notes like "Grandpa, that was the best week of my entire life. I can't wait until we go back to Hawaii together."

Parents are reporting that their children return more mature, confident, and closer to their grandparents than ever before.

I've seen this magic firsthand. Last year, my oldest son did his first skip-gen trip with his grandma to Kauai when he was 10. He flew solo from Seattle – his first time ever – and spent a week with her doing everything from beach days to local adventures. The confidence he gained from navigating that trip independently was incredible, and he immediately asked when he could do it again.

We've also done this with older kids. A few years ago, my teenage niece and nephews (14 and 16) flew from Seattle to meet us and their grandparents on Oahu while their parents stayed home. We gave them their own hotel room right next to ours, let them explore Waikiki independently with their phones, and they joined us for meals and activities. The balance of independence and connection was perfect.

But here's what most families don't realize...

Skip-gen Hawaii trips require different planning than regular family vacations. The accommodation needs are different (everyone needs their own space). The activity mix is different (you need things that work for both 8-year-olds AND 70-year-olds). Even the island choice matters more.

I just spent months researching this trend and talking to dozens of families who've done successful skip-gen Hawaii adventures. The patterns are fascinating, and the strategies that work are very specific.

I created a complete guide covering:

• Which Hawaiian islands work best for different skip-gen dynamics
• Accommodation strategies that prevent meltdowns and exhaustion
• Activity planning that engages both generations (with backup plans)
• Age sweet spots and timing recommendations
• Budget considerations (grandparents typically pay 90% of costs)
• Communication strategies between all three generations

​Get the Complete Skip-Gen Hawaii Guide →​

This trend is just getting started, and the families who understand how to do this well are creating experiences their kids will talk about for decades.

Whether you're a grandparent considering this adventure or a parent wondering if you should suggest it to your folks, this guide walks through everything you need to know.

These aren't just vacations – they're legacy-building experiences.

Aloha,

Marcie

P.S. The optimal age range? 8-12 years old. Old enough to remember everything, young enough to still think grandparents are the coolest people in the world. If your kids are in this zone, now might be the perfect time to start this conversation.