Why August Is the Best Month to Book Your Winter Holidays (Copy)

There is a version of every family trip that exists only in our heads before we leave.

The moments we picture. The photographs we are quietly already composing in our minds before we have even packed.

And then you arrive, and a nine-month-old has a completely different plan.

We were staying at the Four Seasons Wailea on Maui. One of those places that feels almost unreasonably beautiful. The kind of resort where the pool seems to go on forever and the ocean is right there and everything is designed to make you feel like life is very good.

My plan for that morning was straightforward. Get him into the water. Let him splash and kick. Reset the day.

He was not interested in the pool at all. 

What he wanted — with great determination and absolute clarity — was the patch of grass just beside it. Soft, green, perfectly crawlable. He made his way across it slowly, stopping to examine things I could not see, completely absorbed in a world that had nothing to do with the Pacific Ocean behind him.

So I sat down beside him and let him lead.

We stayed there for a long time. No agenda. No next thing. Just a baby on a lawn at one of the most beautiful resorts in the world, deeply content about the grass.

I think about that morning often, especially when I am working with families who are trying to plan every hour of a trip. 

There is a particular stage of parenting where the most valuable thing you can do is follow the child's rhythm rather than the itinerary. Where the unscheduled morning is not a wasted one. It is reading your child well enough to know that two hours of unstructured time is exactly what is needed before they can be ready for anything else.

The best family trips have breathing room built into them. Not every day needs to be the excursion or the experience or the plan. Some of the most important days are the ones where you sit on the grass and let them lead.

Those days never make the highlight reel. But they are often what makes the whole trip work.