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.
I showered, put on comfortable travel clothes—black leggings, a soft Northwestern sweatshirt, the running shoes I use for my four-mile jogs along the lakefront—and double-checked my suitcase one more time. Passport. Wallet. Printed confirmations even though everything is in an app now. My cardiology brain doesn’t trust a single point of failure.
At 5:00 a.m., a black sedan from a local car service pulled up in front of my brownstone. The driver loaded my suitcase into the trunk while I locked the front door of my house that I’d bought years ago when the hospital bonuses were coming in strong and the Chicago housing market was still forgiving.
We drove down Lake Shore Drive toward O’Hare International Airport, the lights of the Chicago skyline shimmering over Lake Michigan, the Willis Tower and John Hancock Building just silhouettes against a still-dark sky. Even after all these years, that drive still makes me feel lucky to have lived my whole life in this city.
We were all meeting at O’Hare at 6:00 a.m. for our 8:15 flight to Honolulu, then on to Maui. Hawaiian Airlines. I’d upgraded all five tickets to business class—lie-flat seats, real silverware, little orchids on the trays. I wanted this to be special.
I arrived at the airport at 5:45, rolling my suitcase through Terminal 3, past the Starbucks with the line already snaking out, past families in Disney sweatshirts headed to Orlando, past bleary-eyed business travelers clutching briefcases and cold brew.
I scanned the crowds near the Hawaiian Airlines check-in counter and spotted them.
Kevin, my thirty-eight-year-old son, tall with his father’s broad shoulders, dark hair starting to show a few gray strands at the temples. The boy I raised alone after my husband, Thomas, died of a heart attack when Kevin was just ten years old.
