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Flying With Winair, A Pleasant, Efficient, Safe Caribbean Airline

Mon, 06 Jul 2026 12:11:07 GMTSource: One Mile at a Time

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.

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
Winair flies DHC-6-300 Twin Otters

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
Winair flies to St. Barts Airport

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.

Winair DHC-6-300 Twin Otter

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.

Winair DHC-6-300 Twin Otter cabin
Winair DHC-6-300 Twin Otter cabin

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

Winair DHC-6-300 Twin Otter cabin
Winair DHC-6-300 Twin Otter cockpit
Winair DHC-6-300 Twin Otter cockpit

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

Winair DHC-6-300 Twin Otter views
Winair DHC-6-300 Twin Otter views

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).

Redeem Flying Blue miles on Winair
Redeem Flying Blue miles on Winair
Redeem Flying Blue miles on Winair

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?


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