Jetset kid

“Ice keem, peez,” Esme instructs the waiter. Lo and behold, a bowl of prettily garnished vanilla ice cream is placed before her (even though her dinner plate was full when it was whisked away). For the next 15 minutes, she quietly eats her dessert with a focus she brings to little else in her two-year-old life. My husband and I actually finish our meals. I would like to stay here forever. Sadly, this isn’t possible, as we are enjoying a mere week of ice cream–bribed good behaviour in the lap of five-star luxury at Half Moon resort in Jamaica.

In my pre-child life, travel used to go like this: a lot of New York, some Paris and a bit of Milan, with a spot of South Beach and a trip down the Nile thrown in for good measure. And those were just the work trips. On my own time, there were jaunts to Mexico, Cuba, Portugal, Spain, Italy…. When my husband and I started dating, he was living in Brooklyn and commuting to Toronto for work. Air miles were built into our relationship right from the start. When we discussed having a child, we told ourselves that we wouldn’t change a thing once we were three. Babies are portable, we told ourselves. And it turns out that they are, but let me tell you, they have a lot of luggage.

After a couple of trips to visit family with our daughter in her first year, we decide it’s time for a real holiday. All of my usual criteria for destinations—important exhibitions, great restaurants, cool bars, cute shops—are derailed by worries over practical issues, like schlepping baby gear, access to safe drinking water and where to find dinner at 5:30. Google “family travel,” and the overwhelming results are resorts that may do a great job of entertaining kids but leave parents nauseous. Click a little further, however, and a fantastic image emerges: stylish family travel. Companies such as Horizon & Co., Luxury Link and Indagare specialize in upscale travel and have begun to turn their attention to travellers with kids. Some offer suggestions and reviews, and some are actual concierge services that will book your entire trip. But the most useful site I came across is ciaobambino.com—a brilliant resource for those who are loath to give up chic but need to face the facts of travelling en famille. The brainchild of Amie O’Shaughnessy, a mother and former frequent flyer, the site features reviews and recommendations of fashionable resorts and villas around the world, and breaks them down into categories by age group. Families jetsetting with teens need trips that give their kids some privacy, while younger kids need reliable sitters so parents can enjoy a late dinner. You’ll also see unsexy but essential details about the extras each property provides, such as cribs, strollers and bottle warmers.

We choose Half Moon resort just outside Montego Bay, Jamaica, for what it offers us as a couple travelling with a toddler but also for its laid-back glamour. After all, Jack and Jackie spent their last pre–presidential race holiday here. (A letter Jackie wrote home to JFK’s secretary outlining what should become of little Caroline in the event that both of her parents die hangs among other memorabilia in the lobby.) Set on 400 lush acres, the resort is made up of guest rooms, suites and villas laid out around the breezy colonial entrance and lobby. You can easily imagine previous guests like Joan Crawford and Clark Gable swanning across the black-and-white checkered marble floors on their way to one of the beachside bars or restaurants. Our villa has many pretty details: a nice, deep tub, in case you don’t get enough soaking in the ocean; a lovely terrace with a big table for alfresco dining; a large, romantic bed; and all the services you’d expect at a good hotel, such as housekeeping and room service. But two features make it perfect for us: a small kitchen (staying somewhere without a fridge may be possible for some families, but their children probably don’t bellow from their cribs in the night: “Bottle! I want bottle! Peez!”) and a good-sized living room where we can enjoy a bottle of wine after our girl falls asleep upstairs.