WINAIR Expands Flights to Trinidad

Casey Halston

Published: February 6, 2026 10:00 PM ET

WINAIR has officially expanded its flight services to Trinidad, enhancing connectivity across the Caribbean. The airline now operates flights between St. Maarten (SXM) and Trinidad (POS) twice a week, specifically on Sundays and Wednesdays, utilizing its fleet of ATR 72-500 aircraft.

Details of the New Flights

Route: St. Maarten (SXM) to Trinidad (POS)
Frequency: Twice weekly (Sundays and Wednesdays)
Aircraft: ATR 72-500

During the arrival ceremony in Trinidad, WINAIR CEO Hans van de Velde commented on the deeper connections shared between Trinidad and St. Maarten. He emphasized cultural ties and resilience as key elements binding the two islands.

Significance of the Expansion

The expansion represents more than just flight availability; it aims to strengthen regional ties. Eli Zakour, Trinidad and Tobago’s Minister of Transport and Civil Aviation, acknowledged this moment as crucial for regional air connectivity, expressing gratitude to WINAIR’s management and staff for their commitment to enhancing travel options.

Comparing Airlines

WINAIR will be competing with Caribbean Airlines, which currently offers three non-stop flights weekly between St. Maarten and Trinidad on Mondays, Fridays, and Saturdays. Additionally, Caribbean Airlines provides a Tuesday service that includes a stop in Barbados.

Fare Options with WINAIR

Saver Fare: Lowest cost; only includes a personal item.
Lite Fare: Includes a carry-on bag.
Prime Fare: Allows for both a carry-on and checked bag, thus providing maximum flexibility.

Travelers should consider these fare options carefully. For those traveling light, WINAIR’s Saver and Lite fares offer economical choices. However, passengers needing more baggage should opt for the Prime fare for convenience.

Other Caribbean Developments

WINAIR has been actively increasing its route offerings. Aside from the new Trinidad flights, the airline launched new connections between Barbados and St. Kitts (SKB) in January 2026 and increased flight frequency from Tortola (EIS).

Additionally, Trinidad will welcome InterCaribbean, which is set to launch four weekly flights to Barbados starting on March 8. This service will be operated with ATR 72-600 aircraft, further intensifying competition in the region.

Future Opportunities

The Trinidad and Tobago government is also exploring opportunities to establish flights to Ghana. Minister Satyakama Maharaj announced that a Ghana Air Services Agreement is in the final stages, aiming to facilitate chartered services with Ethiopian Airlines between Trinidad and Accra (ACC).

This initiative could potentially position Trinidad as a transatlantic hub, paving the way for increased travel opportunities and connectivity in the future.