Winair’s Homecoming Flight: Sint Maarten to Port-of-Spain

Winair Makes Inaugural Sint Maarten–Port-of-Spain Route a Homecoming Moment for Crews

In a milestone marked by both professional achievement and personal longing, Winair’s inaugural flight from Sint Maarten to Port-of-Spain touched down with a sense of déjà vu for two Trinbagonian aviators who have long dreamed of flying home.

Capt. Michael Awai, a 40-year-old director of flight operations, check pilot, and ATR instructor, and First Officer Shane Pinheiro, 28, Winair’s Flight Operations Engineer, have been flying together on and off since October 2019. The pair, who have spent years navigating the skies of the northern Caribbean and operating some of the region’s most technically demanding airports, finally executed the opportunity they’d hoped for: piloting Winair’s first commercial flight connecting Sint Maarten and Trinidad.

The journey began with a scenic ascent where Awai, flying the ATR 42-500, served as an unofficial guide to the 45 VIPs, officials, and tourists aboard. As the aircraft approached Port-of-Spain’s horizon, Awai focused on precision and a smooth approach, carefully steering through the local weather and terrain. Pinheiro, meanwhile, monitored instruments from the right-hand seat, ensuring the flight remained well within the airline’s safety margins.

On the ground, a chorus of media, officials, and airport personnel watched the momentous occasion. Among them were Karen and Ryan Pinheiro, Shane’s mother and father, whose pride was palpable amid the midday heat.

“I cried, yes, absolutely! Oh God, I am so proud; you don’t understand,” Karen told Guardian Media. While Pinheiro has spent seven years with Winair, his mother has long been his unofficial co-pilot—an anecdote he recounted with a smile. “I have flown with him before, right here in Piarco, many years ago, when he was training to get his license. He had me do some stop-and-goes at night with him, which was a little daunting because he was only 16 at the time,” she recalled.

For Awai and Pinheiro, the Trinidad leg represents both a personal homecoming and a professional milestone. “Feels good, you know, it’s one of those bucket-list items to tick off—growing up you always want to fly to where you started,” Pinheiro told Guardian Media.

The official welcome ceremony underscored the broader significance of the new route for the region. Hayden Newton, General Manager of Airports Authority of Trinidad and Tobago (AATT), called it the “culmination of countless years of courtship, collaboration, careful planning, and shared intent.” Transport and Civil Aviation Minister Eli Zakour—a commercial pilot himself—emphasized aviation’s role in Caribbean development, noting that new connections “improve access, support trade and tourism, and expand travel options for our citizens. For businesses, it creates new commercial opportunities.”

Trade, Investment, and Tourism Minister Satyakama Maharaj highlighted the potential for multi-destination travel, saying the route could drive higher-value visitor arrivals for regional festivals, conferences, and events, while strengthening passenger flows between the Northern Caribbean and the Southern Caribbean.

For Pinheiro, the flight is also about something deeply personal: a chance to be home more often. “I miss the food and culture,” he said with a grin. For Shane’s parents, Ryan and Karen, the inaugural flight marks more opportunities to see their son—the calm, capable pilot they’ve always believed in—more frequently.

As Winair’s ATR-42-500 finds its new rhythm on the Sint Maarten–Port-of-Spain corridor, Awai and Pinheiro’s homecoming story adds a new chapter to Caribbean aviation history—one that combines professional excellence with a heartening reminder of the ties that bring pilots back to where their dreams began.

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