On our flight from Toronto to Sint Maarten, a mother asked if I’d switch seats so she could sit with her two boys. I agreed, ending up next to her husband—in premium class—and, without meaning to, in the middle of a beautiful tourism story.

For him, Sint Maarten isn’t just a destination. He first came here as a boy with his parents. Now, he brings his sons, aged 13 and 15, every year. They stay in the same spot, just on the other side of the airport, in a bay overlooking the beach, with restaurants and life in every direction. The staff has known him for three decades, watched him grow up, and now welcome his children like family.

Even their clothes spoke of ease: both parents in loose drawstring trousers—hers pink, his grey—the kind you could imagine them wearing at home. The boys, in summer shorts and T-shirts, looked like any kids on school break. Dad even knew, to the second, when the aircraft would park and the engines shut down. Part of the magic, he said, was stepping off the plane and, within minutes, feeling the warm air, hearing the surf, and being where they belong—no friction, just an instant welcome.

Over time, they’ve refined the art of coming back. When the boys were younger, they stayed in all-inclusive resorts: predictable, convenient, and, as he put it, a little confining, but reassuring for a protective mother. Now, comfortable with the island, they prefer the flexibility of a timeshare: the freedom to cook, grab takeaway, or eat out—and the numbers still work out the same, only better.

A Known Quantity

Their trips have a rhythm. A shared charter to St. Barts—sailing boat after sailing boat in the harbour—was expensive to get to but worth it, especially when split among 16 friends. St. Barts (officially Saint Barthélemy) is posher and pricier; Sint Maarten shares the ‘expensive to reach’ part, but not the cost once you’re there. Knowing the island well makes it easy to enjoy fully and spend wisely: roadside fried chicken instead of restaurants every day, choosing when to splurge, when to wander. Anguilla, lovely and quick, is their regular boat trip.

His wife and he have a playful, easy dynamic. He would walk back to check on them; she would come forward to use the business section bathroom, once bringing their younger boy to show him how to lock the door. A senior cabin crew member reminded her that two bathrooms in the back were available, but he told her firmly she was allowed to use the front—and she did, though a little sheepishly.

He smiled when he said the boys were gentle, kind, well-behaved. Strangely, the older was the more fragile; the younger, he thought, could travel anywhere alone. He was fortunate, he said, they didn’t get into trouble—and he didn’t think they needed anyone sitting beside them, a nod to the fact that she had traded seats to be with them. She prefers safe; he wants them to grow. This year, the boys have their own holiday money, and if it’s gone in two days, so be it, though I suspect their father will soften any hard lesson.

Familiarity and Freedom

When the azure waters of Sint Maarten appeared below, the cabin changed. Applause broke out, and children pressed to the windows. The plane was packed—perhaps 10% of the passengers were children—and I wondered how many other generational stories were onboard.

At the place they stay, those ties are unmistakable. Many of the same families who once holidayed alongside his father in the same timeshare still return today. His father began the tradition; he’s carried it forward—even if, during the boys’ younger years, they detoured into the predictability of an all-inclusive, no doubt at his wife’s urging. Now they’ve come full circle to the timeshare, where familiarity and freedom meet in a welcome that feels timeless.

And yet, even after thirty years, there is still more to see. On a recent trip, they set out in their rental car to take stock of all the new construction—and in the process found magical places they’d never noticed before. The same instinct has taken them to St. Barts by charter, Anguilla on a whim, and roadside kitchens for fried chicken. So when he mentioned he’d heard Curaçao was worth visiting—sprawling, not quite like Sint Maarten, but with its own charms, including a fine cruise port—it felt like the natural next horizon. Not a replacement for the island he calls home-away-from-home, but a reminder that curiosity and loyalty can live side-by-side.

As a Seychellois and a former tourism director, I recognize this instantly. This is the gold standard: when a place becomes part of a family’s story, and that story keeps going—passed down with the same love, the same return, the same sense of belonging.

Sint Maarten, you’re doing it right.