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. The most common way to travel to and from St. Barts is to fly with Winair.
While there’s not that much to write about when it comes to the inflight experience on a 10-minute flight (there are no pre-departure drinks, hot towels, or mixed nuts!), I did want to talk a bit about the airline in general, plus share my overall experience, as the airline operates some unique routes.
As I see it, Winair is a very safe and reliable airline, though don’t expect much when it comes to customer service (if you want a more luxurious experience in the Caribbean, take a look at Tradewind Aviation). There’s even a points angle to the airline, but don’t get too excited about the value of that.
In this post:
The basics of Winair’s fleet & routes
Winair, which is an abbreviation for Windward Islands Airways International NV, is an airline based at Princess Juliana International Airport (SXM) in Sint Maarten. The airline is owned primarily by the government of Sint Maarten, with the central Dutch government also having a small take. The carrier has been operating reliably since 1961, so it has quite some history.
Winair currently has a fleet of nine aircraft, including:
- Four ATR 42-500s, which can seat 48 passengers
- Five DHC-6-300 Twin Otters, which can seat 19 passengers

The airline operates short haul flights from Sint Maarten to well over a dozen destinations in the Caribbean. Just to call out a couple of especially cool flights for aviation geeks:
- Winair’s most frequent route is the short 20-mile hop to St. Barts (SBH), which is considered one of the most challenging airports in the world to land at
- Winair also operates the 28-mile route to Saba (SAB), and that airport has the world’s shortest commercial runway, at just 1,312 feet

The airline also operates service to airports like Antigua, Aruba, Bonaire, Curaçao, Nevis, Tortola, and more.
Winair has a flawless safety record
Many people considering booking with Winair may have never heard of the airline before, and wonder if flying with the airline is safe. I’ve written in the past about my take on airline safety ratings, and why it’s not something I pay much attention to. Nonetheless, I know it’s something others consider.
Along those lines, I think it’s worth acknowledging that in its roughly 65-year history, Winair has never had a fatal accident. That’s impressive, especially when you consider some of the challenging airports that the airline flies to.
While of no consequence, here’s a fun fact for aviation geeks. Winair isn’t regulated by the European Union Aviation Safety Agency (EASA), but instead, is primarily regulated by the Department of Civil Aviation, Shipping and Maritime Affairs (DCASM), which is the civil aviation authority of Sint Maarten.
My experience flying with Winair
I’ve flown to and from St. Barts on Winair, so let me share a few takeaways from the experience, including about the airport experience in Sint Maarten:
- The airline leaves from the main part of the terminal, so you’ll see the Winair check-in counter next to all the other airline check-in counters; then all Winair flights depart from the same part of the terminal, which can be quite chaotic, since there are sometimes multiple flights departing around the same time
- If you’re just connecting at Sint Maarten Airport, you can make an airside transit in both directions (by just clearing security), as long as you have your boarding pass for the connecting flight; if you don’t have your boarding pass, you’ll have to clear immigration and go to the check-in counter
- Definitely be aware of the baggage limits with Winair, since different fares have different baggage allowances; those limits are pretty strictly enforced, given how small these planes are
- Winair seems to be pretty good about letting passengers stand by for a different flight; there are constant flights between Sint Maarten and St. Barts, and they’ll typically let you get onto an earlier flight, as long as seats are available
- Winair has open seating onboard, so if you have a particular seat preference (like sitting in the front of the Twin Otters right behind the cockpit), you might want to be a bit pushy, or whatever
- Don’t expect anything amazing when it comes to service on Winair, as I find the ground staff to be uniformly indifferent
The flights to and from St. Barts are all operated by DHC-6-300 Twin Otters, and you board through the rear of the aircraft.

The plane has 19 seats, with the cabin arranged in a 1-2 configuration. There’s no door between the cockpit and cabin, and even non-aviation geeks seem to take a lot of pictures and videos on these flights, given the views.


Sitting right behind the cockpit is such a treat, since you can see all the action.



But even if you don’t have a view of the cockpit, the perspective out the cabin windows are equally beautiful…


As I see it, Winair is a great airline when things go right, and if you don’t need a lot of help. However, definitely manage your expectations when it comes to service from the ground staff, as they aren’t overly helpful, in my experience.
Also, while I’ve never had irregular operations with the airline, reports suggest that the airline handles these very poorly. I guess I’ve been lucky by not having faced that myself.
Earning & redeeming miles on Winair
Winair is a fully independent airline, and doesn’t have its own frequent flyer program. The airline does have interline agreements with a variety of airlines, ranging from Air Caraïbes, to British Airways, to Delta, to United. An interline agreement simply means you can book a ticket that includes travel on both airlines, and it’s not necessarily indicative of a larger partnership.
Winair’s closest partnership is with Air France-KLM, which isn’t surprising, given the Dutch and French ties. The good news is that Winair participates in the Flying Blue program. You can earn and redeem Flying Blue miles for all Winair flights, which is great.
Unfortunately when it comes to redeeming miles, don’t expect you’re going to get some amazing value. One-way award costs seem to range from 14,000 miles to 33,500 miles, depending on the route. That doesn’t include the taxes and carrier imposed surcharges, which typically range from $75 to $125 one-way, give or take.
Unfortunately that doesn’t represent a great deal, given that you typically won’t get more than one cent of value per mile for Winair tickets (and sometimes significantly less than that). However, award availability is good (probably for the above reason).



Bottom line
Winair is a nifty little airline that’s based at SXM, operating flights to nearby Caribbean islands. The airline serves some of the world’s coolest airports, from St. Barts to Saba. I’ve had good experiences with the airline, in terms of them operating reliably, and there’s no arguing that they have a great safety record. If you’re considering a flight with Winair, I’d have no qualms recommending the airline. The only thing I’d note is that don’t expect much from the ground service or service, but then again, that’s pretty typical in the Caribbean.
If you’ve flown with Winair, what was your experience like?
If I hadn't come to trust OMAAT over many years, I would suspect this is a sponsored post though it is similar to one you wrote in 2023. Ben, Have you read the reviews of Winair? They are notoriously unreliable with terrible customer service in the event of frequent delays and flight cancellations. Jason, who posted his experience, is similar to my own trying to get out of St Bart's, expect in my case, it...
If I hadn't come to trust OMAAT over many years, I would suspect this is a sponsored post though it is similar to one you wrote in 2023. Ben, Have you read the reviews of Winair? They are notoriously unreliable with terrible customer service in the event of frequent delays and flight cancellations. Jason, who posted his experience, is similar to my own trying to get out of St Bart's, expect in my case, it was impossible to get a refund despite their cancelling the flight. I ended up just using my travel insurance to compensate for the additional costs of booking a taxi and ferry to get to St. Maarten.
It has a whopping 2.5/5 on tripadvisor with 163 out of 275 reviewers rating them as "terrible". Other reviews on trustpilot, airlinequality and reddit are similarly bad. I'm very glad you've had good anecdotal experiences, but I suggest you add some context of the broader consumer sentiment toward the airline.
If the passengers had not crowded into a 13 seat airplane , everything would have been cool . One would not be "trying to get out of St.Barts" , if one had not gone amongst a large mob . WinAir was correct in cancelling the flight if passengers don't control themselves .
I don't know what you're talking about. My experience with WinAir was 2 years ago and there was no 'large mob'. It was cancelled before I had gotten to the airport.
@ Justin -- I appreciate the other perspectives, and I added something to my post about that. I've only had on-time flights with the airline, but it's clear that when there are irregular operations, it's pretty unpleasant (which isn't surprising, based on the indifference I've noticed among ground staff). Looking at Flightradar24, I'd say the airline generally operates quite reliably, in the scheme of things, especially for the Caribbean. But of course when things go...
@ Justin -- I appreciate the other perspectives, and I added something to my post about that. I've only had on-time flights with the airline, but it's clear that when there are irregular operations, it's pretty unpleasant (which isn't surprising, based on the indifference I've noticed among ground staff). Looking at Flightradar24, I'd say the airline generally operates quite reliably, in the scheme of things, especially for the Caribbean. But of course when things go wrong, that doesn't get you far!
I'm glad you had a good experience with them. Mine was not quite that good.
First, they're simply not always reliable. People in St. Maarten refer to it as "When Air" - as in who knows when the flights - or if - will go. That's my experience precisely.
I was going to St. Barth's for the first time in April - flew into SXM from IAD on United and was supposed to connect to...
I'm glad you had a good experience with them. Mine was not quite that good.
First, they're simply not always reliable. People in St. Maarten refer to it as "When Air" - as in who knows when the flights - or if - will go. That's my experience precisely.
I was going to St. Barth's for the first time in April - flew into SXM from IAD on United and was supposed to connect to SBH on Win Air. On let's say a flight at 3PM. Well, as you note, the gate area for Win Air at SXM can be chaotic. There were multiple flights that afternoon as it was a Saturday. Lots of people. TLDR, my 3pm flight kept getting delayed (as did many others), people bribed their way on to earlier flights (I saw multiple instances of people just handing $100 bills to the staff to get their parties on the earlier flights that were leaving late), and eventually, around 5:30PM, they announced all flights for the rest of the day were canceled, stranding a good 50-60 people who had been ammassing there all afternoon. What followed was a frantic dash to get luggage, ask at the Win Air desk for rebooking (nothing available for the next two days, we were told)., then a frantic pairing up with other stranded passengers to take taxis to the ferry dock for the last ferry to Saint Barth. It was mayhem, but at least I got to St Barth rather than be stranded over night in SXM. To their credit, I wrote to their cusotmer service the next morning and was promptly issued a refund for the outbound portion, but still. It was stressful, and, as you point out, service was indifferent.
My flight back from SBH to SXM was scenic and on time, though. So... it works, but be prepared for chaos. Several people I talked to in the gate area all mentioned that it was always chaotic and all recommended to go through San Juan on Tradedwinds as an alternative (but that's SIGNIFICANTLY more expensive....)
Alas, I agree, - it's a neat little airline when it works, and SBH is a great place. I enjoyed my time there.
Obviously , too many passengers , crowding in to a 13 seat airplane , was the cause . Passengers ought to have controlled themselves and not all gone at once . Rather than crowding in , they ought to limit their numbers to the 13 seats on the airplane . duh .
@ Jason -- Yow, that sounds pretty awful, especially the bribing part, if that's what was really going on. I've only had reliable flights with them, so obviously can't speak to that, but I added a note to the post about the airline probably not being great when there are irregular operations.