My brood’s annual multigenerational trips, which have included spending a week at Palmetto Bluff in South Carolina and taking over a lakeside cabin in Maryland, are always a highlight of my year. But planning meals and coordinating activities for a group that ranges from toddlers to septuagenarians is an exercise in military-level coordination. Not long ago we tried something new in the hopes of lessening the madness: a cruise. My mother and I joined my sister, her husband, and their two boys, then ages five and seven, on a New Year’s Eve sailing with Disney Cruise Line. I’m someone who has had to finagle last-minute dinner reservations for 14 and search desperately for a pontoon boat that could hold everyone, so I appreciated all the little things about cruising that made it easier to relax. Like not needing to plan ahead in order to eat dinner together during peak hours. Or, just as novel, not having to eat together at all—my mother would order coffee to sip on her balcony while I shamelessly hit the breakfast bar hours after my nephews had eaten.
Because we were sailing with Disney, which applies its park expertise to the cruise experience, we didn’t have to think about entertaining two young kids, either: There were screenings of new movies and character meet and greets, in addition to the kids club. The excursion to Castaway Cay, the line’s private island in the Bahamas, was a stark contrast to beach days of vacations past. We walked directly off the ship and made our way onto the sand. There were plenty of umbrellas, floats, and places to eat. No one had to wake up at dawn to reserve lounge chairs. No one threw their back out dragging an enormous Yeti packed with a stash of cold drinks. This sail was the perfect way to reset: We still had our family time, and no one had to wash a single dish.
This article appeared in the August/September 2020 issue of Condé Nast Traveler. Subscribe to the magazine here.