Three-time Olympic beach volleyball gold medalist Kerri Walsh Jennings has just shared the details of a family trip to Kauai with her husband Casey and their three teenagers — Joey, 17, Sundance, 16, and Scout, 13 — and it doubles as a surprisingly useful template for anyone travelling with kids on the cusp of flying the nest.
The island already means something to the family: they honeymooned there in 2005 and have returned several times since. But this trip, Walsh Jennings says, felt different because the window is closing. With three teens pulled apart by sport, school, training and friendships, she and her husband wanted one of the remaining stretches of uninterrupted time together before the kids' worlds expand beyond easy reach.
What's striking is how little persuasion the teenagers needed. She expected a typical adolescent request for independence; instead they leaned in — hunting for hidden beaches and trails, chasing down the best shaved ice, surfing, snorkelling, and playing games on the lawn above Hanalei Bay. Nobody reached for a phone on that first evening, watching the sunset. Her read: teenagers still crave connection and simplicity, maybe more than ever, it just looks different than when they were small.
Days followed a loose, deliberately slow rhythm. Active mornings — surf, swim, hike through the island's interior — balanced against long dinners that stretched into long conversations, slow coffees on the balcony, and a nightly sunset walk as a family ritual. A local market was her favourite repeat stop. The conversations went deeper than usual, she says: dreams, fears, growing up, purpose, what kind of people they want to be. Away from the usual distractions, people open up differently.
Her takeaway for parents of teens is blunt: just book it, and don't try to get it perfect. Over-scheduling is the enemy — leave room for wandering, resting and spontaneous detours, and let the island set the pace. Above all, put the phone away and actually watch your kids. For an athlete whose career was built on being fully present under pressure, Kauai offered presence for no reason at all, and she calls those fleeting family moments the real gold.
For travellers, the useful core here isn't celebrity trivia — it's a philosophy that suits Kauai specifically. It's the greenest and most laid-back of the main Hawaiian islands, better suited to slow mornings, farmer's markets and uncrowded north-shore beaches than resort bustle. A week built around a handful of anchors (a surf lesson, one good hike, nightly sunset walks) tends to beat a packed itinerary, especially with teenagers who need a bit of autonomy to enjoy themselves.
