For those who want to island hop in the northern portion of the Caribbean’s Lesser Antilles, there are few options. One can take a ferry. Or one can fly. And while ferries can be ok for especially short trips, most island hopping necessitates a flight, either because distances are too far for day trip realistic possibilities or because one doesn’t want to lose half a day or more each way for some sort of overnight or multi-day side trip.

The best home base for exploring this part of the Caribbean is the split island of Sint Maarten/Saint-Martin. Not only does the island offer a ton to do (just click that link above to read all of my content about the island), but it also has direct flights into its Princess Juliana International Airport from all over the eastern US, Toronto, Montreal, Amsterdam, and Paris.

But you want to explore other islands, and not just Anguilla (for which you’ll probably take the ferry). Enter Winair, literally Windward Islands Airways although these are the Leeward Islands. Based here in Sint Maarten, Winair connects this island hub with several other cool islands in the region.

Winair was founded in 1961 here in Sint Maarten, meaning the airline is celebrating 65 years this year! And to be in business that long, they must be doing something right.

This was my first time on WinAir, taking the 18 minute long flight from Sint Maarten to Sint Eustatius, a Dutch island to the south. And I’d like to offer you an honest review of the experience.

Booking

Booking on Winair is easy, and pricing is in US dollars, which makes things easier for the largely American tourist base to Sint Maarten. (And both that island and Sint Eustatius use the dollar as their unofficial currency.)

It should be noted that my flight times changed at least once or twice each in the few months between booking and flying, the result of a changing schedule. But with multiple options daily for even a destination as tiny as Sint Eustatius, it wasn’t an issue.

Check In

Online check in was a breeze, and I arrived at the airport in Sint Maarten with my boarding pass already. I did, however, still head to the desk to have my carry-on suitcase checked. Winair operates only small turbo-prop aircraft, and it’s rare that one can fit anything in the overhead, if there even is an overhead compartment.

Boarding

My boarding pass said boarding would begin a half hour before departure. So I was a bit surprised when, sitting in the lounge, my name was called an hour prior to departure – a half hour before the listed boarding time. In fact, I believe every passenger was summoned to our gate via the loudspeaker.

So I quickly packed up my stuff, headed to the gate, showed my boarding pass and ID, and was led to a waiting area. Here I waited about ten minutes until the remainder of the passengers had done the same, and then we boarded a shuttle to our waiting plane.

Winair planes are small. They operate two types. The ATR 42 says it holds just under 50 passengers. I see a couple of those parked on the tarmac.

My plane was the much smaller, roughly 20 seat, DHC-6, and upon arriving to it, we lined up to climb the small stairs in. (If one cannot climb stairs, one cannot get into this aircraft, I don’t think.)

Inside, it is apparent why there are no assigned seats. One takes a seat as best as one can. There are no overhead compartments, and not much of an area under the seat in front. Tall passengers struggled to make it into a seat, and ended up sticking into the tiny “aisle” on the single seat side (there is a double on the other side).

Flight

As you might expect given the boarding situation above, we took off early. Yes, early. By almost a half hour. This is a first for me in my flying experience, and a cautionary tale with Winair to definitely arrive with ample time.

Time in the air was a brief 18 minutes, which is both good in that the flight is hot and noisy so less time is better, and bad in that being on a tiny plane, and especially sitting in the front row like I was with a view into the cockpit, is pretty fun!

We flew low, at about 3500 feet (I could see the altimeter), and watching the two pilots operate the plane was fascinating. I only wish I’d had a headset to listen as well, since the noise of the propellers was too loud to hear even from the first row.

The flight was pretty smooth, and landing was easy, even in the wind that is common here.

So What’s the Verdict?

Would I fly Winair again (other than my upcoming return trip to Sint Maarten, which of course I will be taking)? I absolutely would. (The return flight was also easy, since I’ve now taken that.)

Is Winair a good choice for you? That’s a bit more complicated.

If you are not afraid of small planes, are of a reasonable body size, and possessing of enough mobility to traverse the aforementioned stairs and close quarters, Winair can be a great choice for you to island hop. If any of those things are not the case, then maybe not, at least not on the tiny planes. (One can maybe ask which routes Winair serves with the larger ATR 42, which probably makes mobility and size less of an issue, although not removing those completely.)

And if you are a lover of all things flying as I am? You’ll have the most fun flight of your life! Just sit in the front.

Full disclosure: Winair was gracious to sponsor my flights between Sint Maarten and Sint Eustatius so that I could spend a couple days on that second island to write. I made no agreement with them to produce content of any sort, so this article is 100% my own personal experience. And thank you to Visit Sint Maarten for making the connection!

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