I fly planes into one of the world’s most challenging airports to land.
Tradewind Aviation, Mariette Williams
Mike Stein is one of 31 Tradewind Aviation captains qualified to fly passengers into St. Barts.
The tiny Caribbean island is famous for its challenging airport landing.
Sitting between a steep ridge and the sea, pilots can’t see the runway until the last moments.
This as-told-to essay is based on a conversation with Mike Stein, the Caribbean region’s chief pilot at Tradewind Aviation and a trainer for landings at St. Barts’ Gustaf III Airport. It has been edited for length and clarity.
My obsession with the skies started at a young age when my parents signed me up for a 15-minute demo flight with Young Eagles.
Now, I’m among the pool of qualified pilots to fly into Gustaf III Airport in St. Barts — a tiny Caribbean airstrip known for one of the world’s most challenging approaches in commercial aviation. Only a few dozen captains at my company are allowed to fly the approach.
The roughly 2,100-foot airport runway sits precariously between a steep hilltop ridge and the sea, and can only handle smaller planes. Pilots must fly a low, precise approach over the hill before descending quickly to stick the landing, while simultaneously battling rapidly changing crosswinds and rough turbulence.
The training is intense, but I love the thrill of “The Hill.” Here’s what passengers don’t see during the extreme approach .
Landing in St. Barts is like threading a needle
I work for Tradewind Aviation, a US scheduled charter carrier, which operates its St. Barts flights with Pilatus PC-12 turboprops. Only smaller aircraft can use the island’s short runway; large Boeing and Airbus jetliners cannot.
St. Barts is known for being a playground for celebrities and billionaires.
Tradewind Aviation
For passengers, the landing may look daunting. For us, it’s the result of years of training and trusting our judgment. As of 2026, Tradewind has 31 captains qualified to land in St. Barts , with an average of more than 3,000 flight hours.
The approach is visual: It’s hands on the yoke, eyes outside, and feeling how the wind is affecting the airplane. Because of the unique steep descent over the hilltop, the runway stays hidden until the final moment.
As you pitch smoothly down over the crest, the runway appears, framed by the bay. The landing in St. Barts is all about energy management; once you can feel that sensation, it becomes much easier to control the approach.
Inside the cabin, passengers enjoy hillside views as the aircraft makes a scenic, low-altitude approach to the tarmac. We leave the cockpit curtain open so passengers can watch the pilots work.
The runway is short and leads into the bay.
Mariette Williams
The best St. Barts pilots are those with solid stick-and-rudder skills, and those who can self-critique their approaches, as no landing is the same on the island. I want pilots thinking about what they did well, what could have gone better, and how to adjust for the next flight.
Still, we never force a landing, and there are conditions under which we simply can’t land.
If crosswinds exceed the aircraft’s limits, there’s very heavy rain, too much standing water on the runway, or the aircraft is too fast or too slow, we’ll go around or divert for safety.
Training is intense, and not every pilot qualifies
At Tradewind, where I’ve been the Caribbean region’s chief pilot for three years and am a St. Barts flight instructor, several of our pilots regularly fly in and out of the island.
It’s the natural progression if you’re in the Caribbean at Tradewind. Between the descent and wind at the airport, we put our pilots through extensive training, but not everyone makes it through.
We only let captains land in St. Barts, so they’re already very familiar with flying the PC-12. And the training has to be hands-on.
There’s a certain amount of clout that comes with landing in St. Barts.
Mariette Williams
While full-motion simulators used at major airlines can recreate the look of St. Barts, no simulator can truly replicate the sudden wind shifts and intense turbulence of the actual approach.
To train, we put them through steep-approach drills at standard airports so they can master the physics and feel of the intense descent long before they touch down on the island. Next is live training in St. Barts, where pilots perform dozens of landings and approaches.
There isn’t a set time for training. We determine when the pilot is ready and usually give them as much time as they need to figure it out. As long as they are improving while we’re instructing, we’ll keep training them.
The tiny airport in St. Barts.
Mariette Williams
For those who make it, landing in St. Barts is a very exciting approach. It’s fun for everyone on board, especially the pilots.
Passengers will probably feel some bumps, but that’s part of the charm.
Read the original article on Business Insider
