TRINIDAD & TOBAGO--Winair’s planned entry into the Trinidad and Tobago market was the subject of a recent Trinidad & Tobago Guardian business feature, which reported that the St. Maarten-based carrier will begin nonstop, twice-weekly scheduled service between Piarco International Airport (POS) and Princess Juliana International Airport (SXM) on February 1, 2026.
The Guardian report by journalist Brent Pinheiro stated that Winair will initially operate the route on Wednesdays and Sundays, using the airline’s 48-seat ATR 42-500 aircraft. The article noted that schedules are designed to support connectivity via St. Maarten, with onward links to eight Caribbean destinations and additional international connections.
In the interview, Winair CEO Hans van de Velde described the launch as a deliberate first step, signaling interest in increasing frequency and adding routes over time while avoiding overexpansion. He told the Guardian: “It’s a start with only two flights a week. But it’s literally a start. Our intention is to fly more often. And our intention is also to open up more routes. But we don’t want to (make) the mistake other airlines have made in the past, wanting to go too fast. So, we (will) do it steadily. And if success is there, and we think it will be there, we will grow.”
The Guardian feature reported that Winair, after facing serious financial strain in prior years, is now posting strong operating results, including a 16 percent increase in scheduled capacity, a 22 percent increase in passenger loads, and 28 percent growth in total revenue in the first half of 2025 compared to the same period in 2024.
The article also attributed part of the airline’s operating model to its fleet mix, describing five De Havilland Twin Otters and four ATR 42-500s supporting service across 17 countries and 30 destinations, with aircraft size matched to short runways and route demand. Van de Velde explained, “For many routes, for instance, between St Kitts and Antigua, a 50-seater is about the max you can fill. So even a 70-seater would be too much.”
Winair's management view was emphasized: punctuality is central to Winair’s value proposition, particularly because a significant share of passengers connect onward through St. Maarten. Van de Velde told the newspaper: “They connect from, for instance, Trinidad to St. Maarten, but onwards to either the United States or to other islands around us. So, keeping that timing, that on-time performance, that punctuality is crucial for us.”
With regards to the CEO’s position on fares and the regional cost structure, including taxes. He said: “It’s impossible in this region to operate for low prices, because running an airline here is expensive, and there are a number of reasons. One is that there are very high taxes,” adding that on an introductory US$200 one-way fare, “literally half of it is tax.”
Note was also made that Winair’s existing interline relationship with Caribbean Airlines could be expanded, with talks underway toward a potential codeshare arrangement. Van de Velde told the paper: “We already have an interline cooperation with Caribbean Airlines. And we have been in talks for a few months about upgrading that to a codeshare agreement. And I think I can say that I foresee that happening this year.”
The report described the Port of Spain route as a long-term market entry, with Winair anticipating early-stage costs tied to marketing and startup operations. Van de Velde told the Guardian: “This is for us a long-term project, we have a substantial marketing budget and we will probably lose quite some money (in) the first months, but we think we have a place in the market.”
Operational considerations for ticket purchasing in Trinidad and Tobago was considered, including foreign exchange constraints, and cited the airline’s discussions with travel agents and distribution channels to ensure access.
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