The Romance of Flying (and the Airline That Refuses to Let It Die)
Calm lounges, luxe destinations, and the rare airline that still cares about the journey.
I’ve flown with Tradewind Aviation enough times to know their magic trick: they make flying feel like something you want to do, rather than something you have to do.
It starts the moment you hand over your bags and step into their lounge. No shouting. No chaos. No “sir, that water bottle is a threat to national security.” Just calm, civility, and the faint suspicion that you’ve somehow slipped into a parallel universe where travel is designed by people who’ve actually traveled themselves.
By the time you stroll across the tarmac to the plane (the Swiss-made high-performance Pilatus PC-12), you’ve already shed the heavy cloak of everyday nonsense. And if you’re heading to St. Barth? Forget it. That approach alone is worth the trip…descending toward the island, over the hill, down the slope, wheels kissing a runway that appears only slightly longer than a well-laid dining table. They manage it with ease.
So when I was invited to dinner with one of Tradewind’s cofounders, David Zipkin, this week, it didn’t feel like PR. It felt like finally getting the director’s commentary to a film I’ve watched a dozen times.
We talked destinations…Tradewind is expanding all over the Bahamas, keeping Nantucket connected even through winter, and stitching together some of the Caribbean’s greatest hits: Tortola, Virgin Gorda, Anguilla, and the perennial jewel, St. Barth. It’s a network built with a simple philosophy: go where people dream about. Basically…the kind of routes that make you glance at your calendar and wonder, “Could I run away this weekend?”
There was nothing corporate about it. Just an easy, assured conversation with someone who clearly knows their business inside and out.
We drifted into other parts of the operation too: like pilot training that would make a fighter squadron nod approvingly, safety practices that don’t need to be shouted because you feel them in the smoothness of every flight, their incredible staff, and a philosophy of short-haul flying that goes something like: let’s make this easy AND luxurious.
Sustainable fuels came up too. Framed not as marketing language, but as a meaningful part of how short-distance aviation might unfold in the years ahead.
What struck me most is that Tradewind is always evolving. Still tinkering. Still trying to make the whole thing better. Most airlines seem to reach a point where they decide “that’ll do,” usually around the time they remove legroom (and whatever bit of joy is to be found).
But the real reason I keep flying with them is the rare spark of romance that’s almost extinct in modern aviation.
I’m someone who pays attention to the feeling around a journey: the mood, the build-up, the little moments that make it unique and all worth it. And it’s clear Tradewind does too. They’ve managed to keep that romance intact in a world that mostly forgot it ever existed in the first place.
That dinner didn’t sell me anything.
It simply reminded me:
Flying can still feel fun and extraordinary (if you choose the right airline).