By Madison Leary
Sailing the world is something many people dream about. It’s the kind of dream that usually comes with a long list of conditions attached: after the kids are grown, after retirement, after the mortgage is paid, after life slows down.
For us, that timeline never quite made sense.
We didn’t want to postpone adventure until someday. We didn’t want to live one life now and promise ourselves another later. And most importantly, we didn’t want to leave our kids behind while we chased a dream that mattered to us.
So we made the leap.
We live aboard a 47-foot monohull sailboat with our three daughters — ages 2, 7, and 13 — and we cruise full-time as a family. We homeschool through Florida Virtual School, navigate weather windows instead of carpools, and measure distance in nautical miles instead of minutes.
Is it always easy? Absolutely not.
Is it worth it? Without question.
This is why we chose to cruise with kids, what life actually looks like onboard, and why we believe more families can do this too.
A Life We Chose Together
For most families, the idea of living on a boat with kids sounds overwhelming — cramped spaces, constant logistics, unpredictable weather, and no real escape when tensions rise.
And honestly? That’s fair.
Cruising with kids is intense at times. But it’s also deeply intentional.
Our older girls spent their early years in a traditional home. They went to brick-and-mortar schools, rode bikes in the driveway, and played with neighborhood friends. They experienced what most people would call a “normal” childhood.
