I’d been planning this vacation for six months from my brownstone in Lincoln Park, laptop open on the kitchen island while Lake Michigan winds rattled the windows. I cross-checked school calendars and Chicago weather, pored over TripAdvisor reviews, argued with myself about oceanfront versus partial ocean view, and talked to three different concierges on Maui before I was satisfied.

In the end, I booked us into an upscale resort in Wailea—oceanfront suites, on-site kids’ club, lazy river, the kind of place where families from all over the United States fly in with matching Lululemon luggage and sunhats that say “Mama” in cursive. I arranged luau reservations, snorkeling trips, a helicopter tour of the island, and a special day trip along the Road to Hana.

Ten days of memory-making with the people I loved most. Total cost: forty-seven thousand dollars. Worth every penny, I told myself, to see my grandchildren’s faces when they saw the Pacific Ocean for the first time.

The Meticulous Planning
I didn’t just throw money at a travel agent and call it a day. I curated this trip.

Tyler, eight years old, is obsessed with sea turtles. I booked a special marine biology excursion run by a local nonprofit where kids can learn about honu conservation and watch volunteers tag turtles.