I recently wrote about my experience at St. Barts Airport (SBH), which has to be one of the coolest airports in the world for aviation geeks. While the most common way to travel to and from St. Barts is to fly with Winair through Sint Maarten (SXM), we decided to mix things up on our most recent trip, and fly Tradewind Aviation in one direction.
Tradewind is a fascinating little carrier with a presence in both the Northeastern United States and the Caribbean, and they really offer a great passenger experience, with friendly staff, a lounge (in San Juan), and comfortable Pilatus PC-12 planes. While flying with the carrier isn’t cheap, it’s definitely a nice option to have.
In this post:
The basics of Tradewind Aviation’s fleet & routes
Tradewind Aviation was founded in 2001, and is based in Oxford, Connecticut. The idea is that the company is a Part 135 operator registered in the United States, operating both scheduled and private charter flights.
So in some ways, think of this as being along the lines of JSX, which means it’s technically not an “airline,” as it’s not a Part 121 operator. During the previous administration, there was a bit of a crackdown on this “public charter” concept, but nothing actually came of that.
Anyway, Tradewind Aviation operates a fleet of 38 Pilatus PC-12 aircraft, with another 11 of these planes on order. They are each configured to seat up to eight passengers. The Pilatus PC-12 is an absolute beast of a plane.
While it only has one engine, it’s widely regarded as the most versatile and capable single engine turboprop in the world, and it really has jet-like performance. Now, while I think the plane is incredibly safe, I’ll be the first to admit that flying on a single engine aircraft over a body of water always at least briefly gives me pause, but that’s neither here nor there.
Anyway, Tradewind primarily operates in three regions. The carrier has a base in San Juan (SJU), from which it flies to nearby Caribbean islands, with service to St. Barts (SBH) being the highest frequency market.

Tradewind also has a network between Florida and the Bahamas, with flights out of Fort Lauderdale (FLL) and Stuart (SUA).

Lastly, Tradewind has a Northeast network, primarily centered around seasonal flying to Martha’s Vineyard (MVY) and Nantucket (ACK).

For what it’s worth, we booked a one-way ticket from San Juan to St. Barts for just under $600 per person, which is the cheapest fare you’ll find in the market on Tradewind. That’s obviously not cheap, but:
- Tradewind offers a very nice experience, including a lounge in San Juan, which makes it much more pleasant to wait for flights
- There’s massive convenience to connecting in San Juan rather than Sint Maarten — it’s much more seamless, and the immigration process is easier
- I was able to find award availability in business class from Miami to San Juan but not to Sint Maarten, so there were significant savings there
- We ended up being the only passengers on the flight, so that’s quite a good deal for what turned out to be a private charter 😉
- I love to try new flight experiences, so I was happy to have this opportunity
Tradewind Aviation ground experience & lounge
We landed in San Juan from Miami and had a roughly two-hour layover before our flight on Tradewind, to leave a bit of a buffer. We found the ground experience to be totally seamless. The carrier’s check-in facility and lounge are in Terminal A, which is otherwise used by JetBlue.
Once in the terminal, the signage for Tradewind was obvious, and there was no wait to check-in. The agents were super friendly, and we had our boarding passes in no time.


We were then invited to use the lounge, which is located one level above the check-in area, as that’s also where the private security checkpoint is for Tradewind flights.

Once you’re on the upper level, you’ll find the Tradewind lounge right there.


It’s a bit of a makeshift facility, but ultimately it has all the essentials, including plenty of seating, snacks and drinks, and Wi-Fi (though outlets were limited). Rather bizarrely, for the over 90 minutes we spent in the lounge, we were the only guests. Like, despite the number of flights the airline has, no one else showed up.
So yeah, we had no issues finding somewhere to sit. 😉




The lounge has a self-serve food & drink selection, with a bunch of packaged snacks (both sweet and savory), yogurt, packaged cheese plates, coffee, soft drinks, beer, water, and more.




Once your flight is ready for boarding, there’s a private security channel you can go through (not run directly by the TSA), so that’s pretty seamless, as you’d expect, since there were no other passengers.


Tradewind actually parks its planes on the other side of the airfield, so they have shuttles that drive you to the plane, which are pretty comfy.


I have to note that across the board, I found the ground staff to be super friendly. It was a night and day difference between flying with Winair, on that front.
My experience flying with Tradewind Aviation
Tradewind’s Pilatus PC-12s are some sleek-looking planes. At the aircraft door we were greeted by the first officer, who confirmed we’d be the only passengers. She did a quick safety demo, and explained our flight time of roughly one hour to St. Barts.


The Tradewind Pilatus PC-12s are configured with eight passenger seats, spread across four rows, in a 1-1 configuration. The interiors aren’t anything over the top, but they’re way more comfortable than the DHC-6-300 Twin Otters that Winair flies.


We were also invited to help ourselves to the snack basket and drink cooler in the back of the plane.


I of course took a seat in the front row, so that I could watch all the action in the flight deck. The Pilatus PC-12 is much more high tech than the DHC-6-300 Twin Otter, so it’s fun to be able to watch all of that.

The flight was uneventful, with great views the entire way. I just spent most of the flight gazing out the window, as we passed several islands, and the sea was also gorgeous.


Before I knew it, we were on approach to St. Barts. While that’s always exciting, I have to admit that the Pilatus PC-12 is even more thrilling of a landing at the airport than what you’ll find on the DHC-6-300 Twin Otter. To make a car comparison, the Twin Otter feels a bit more like a pick-up truck, while the PC-12 feels more like an Escalade, so it’s a unique feeling when you “dip” during the approach, especially with the engine in the front.


As you’d expect, the pilots nailed the landing, we made a u-turn at the end of the runway, and then we taxied onto the apron, where we deplaned in no time.


Pretty plane, eh?

Bottom line
Tradewind Aviation is a great little carrier that I recently had the chance to fly for the first time. The operator has a fleet of Pilatus PC-12 aircraft, which it primarily flies in the Northeast, between Florida and the Bahamas, and between San Juan and other points in the Caribbean.
While the carrier’s fares aren’t cheap, they really offer a very nice experience, with friendly service, drinks and snacks onboard, and even a lounge in San Juan.
If you’re going to St. Barts, it’s fastest and cheapest to fly from Sint Maarten on Winair. However, if you’re coming from the United States, connecting in San Juan is so much more pleasant, especially with the seamless Tradewind ground experience.
What a treat this flight was, especially since we had the plane to ourselves!
If you’ve flown with Tradewind, what was your experience like?
Are there any interline agreements, or do you have to buy separate tickets?