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 PlanningI 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.