This Caribbean winter is not arriving as one brand-new long-haul route. It shows up as familiar programs switching back on at different dates. Schedule databases reread on October 4 (FlightsFrom, Directflights, FlightConnections, Flightmapper) confirm part of the picture and correct another part. Between November and March, that gap matters as much as the headline when the arrival day at Princess Juliana is still open.
Miami: two American flights, not three in the current timetables
American Airlines is still the Miami carrier into Princess Juliana. FlightConnections, updated October 4, counts 13 flights a week, about two departures a day, on the Boeing 737 MAX 8. Directflights, current as of September 28, shows 14 frequencies in the week of October 26: two departures every day, around 10:00 and 12:30. Flightmapper lines up two dailies from October 5, AA 2893 and AA 2440, again on the 737 MAX 8. A full winter schedule could reach three flights on some days, as many as 21 rotations. That third flight is not in the timetables reread on October 4. Flight numbers differ from one database to the next: frequency and aircraft are the stable facts, and the time on a chosen day still needs a fresh check.
New York: Delta in mid-November, American in mid-December
JetBlue is already on JFK-SXM, with no seasonal gap showing in the October week. The high-season change is the other two carriers coming back. FlightsFrom and Directflights date Delta's restart to November 14, 2026. The October calendar is empty: the days of that restart are not spelled out yet. The same database associates the Boeing 757 with Delta on this route, the type used through September 5 on the summer Saturday (DL 1887 in Flightmapper). Nothing in that file says November opens as a daily flight.
American steps into the New York market on December 19, 2026, the start date shown by FlightsFrom. Directflights lists those flights on the Boeing 737 MAX 8, leaving JFK Terminal 8. From that date, three airlines are filed nonstop between JFK and SXM, for the stretch of winter when the three schedules overlap. The October grid does not yet show American's days of operation: the date is a threshold, not a timetable.
Toronto and Montreal are not one block
The two useful Canadian airports are Pearson (YYZ) and Trudeau (YUL). From Toronto, FlightsFrom's week of October 12 shows Air Canada twice (AC 2106) and WestJet once (WS 2588). Air Transat is marked from October 31. The three names are on the route, but not yet on the same footing: in early October the total is a handful of flights, not a daily blanket.
From Montreal, Air Transat is already there: TS 284 on Friday in the week of October 12. Air Canada is dated October 31. WestJet is less settled. FlightsFrom files its last YUL-SXM on April 23, 2026, while another schedule read (2LNR) still shows WS 2950 on some Thursdays in October. Until those databases agree, a WestJet winter out of Montreal is not something to count on.
Curaçao: nine Winair departures in the published week
In the week of October 12, FlightsFrom lines up nine Winair departures to Curaçao: WM 805 every day at 7:10, and WM 811 on Wednesday and Sunday. That sits in the nine-to-ten flights a week range repeated on October 1. The ten-flight "winter schedule" figure comes from a Winair release that sites are still reprinting, and the table in it is the 2024-2025 winter. The week on file now is nine. Z Air adds two departures that same week, Wednesday and Friday, which does not change the Winair count.
None of this is locked through March. Carriers often load the Christmas peak later, then drop a flight if the cabins do not fill. A Miami or JFK frequency held for high season is worth rereading, flight number included, in the weeks before departure. The arrival airport remains Princess Juliana (SXM).
Opening photo: American Airlines Boeing on approach to Princess Juliana, over Maho, January 9, 2015. Paul Sableman, Creative Commons BY 2.0.