This wasn’t about my career or my bank account. This was about family. About my son Kevin. His wife Jessica. And my two precious grandchildren, Tyler and Emma.
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. Worth every airline mile, every early-morning call with a travel concierge sitting somewhere in a glass office in Honolulu or Los Angeles.
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.
Emma, six years old, loves princesses and dolphins. I found a dolphin encounter program at a reputable facility, read every review to make sure it wasn’t exploitative, and reserved dinner at a restaurant where she could dress up in a little blue dress and feel like she’d stepped into her own fairy tale. I even ordered a tiny plastic tiara off Amazon, shipped it to my house in Chicago, and packed it in my carry-on.
Everything perfect. Everything planned with love.
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