SIMPSON BAY, St. Maarten – July 8, 2026 – A landmark moment for Caribbean regional aviation took place this week, as Windward Islands Airways International (Winair) unveiled the first aircraft in its fleet wrapped in a custom 65th anniversary livery, officially kicking off a 12-month celebration of the carrier’s six-and-a-half decades of connecting communities across the region.
The commemorative design, applied to one of the airline’s ATR aircraft, features custom anniversary decals that honor the carrier’s historic milestone while reinforcing its longstanding promise to deliver safe, consistent regional air connectivity across the Caribbean. The special branding will be rolled out across the entire Winair fleet gradually over the coming months, turning every flight into a moving tribute to the airline’s legacy that stretches back to its founding in 1961, allowing passengers across its route network to share in the celebration.
Over 65 years of operation, Winair has grown from a small regional startup into one of the Caribbean’s most influential and enduring airlines, serving as a critical lifeline linking dozens of island communities. Beyond simply moving passengers, the carrier supports nearly every core sector of regional life: from powering tourism growth and enabling cross-border business to facilitating access to critical healthcare services, connecting students to educational opportunities, and keeping geographically separated family members in touch. Today, it operates an extensive island network from its Princess Juliana International Airport hub and maintains key strategic partnerships with major global airlines to offer seamless connections between the Caribbean and the rest of the world.
As the national airline of St. Maarten, Winair has left an indelible mark on regional economic development. The carrier employs hundreds of local aviation professionals, sustains thousands of indirect jobs across supporting local businesses, and provides the essential air connectivity that attracts foreign investment, enables regional trade, and strengthens cross-island cooperation. Industry analysts note the carrier’s ongoing work remains a core driver of sustainable growth and economic resilience for every island it serves.
“Watching our first 65th anniversary branded aircraft take to the skies is an incredibly emotional moment for every person who has ever been part of the Winair family,” said Winair Chief Executive Officer Hans van de Velde in a statement marking the launch. “This 65-year milestone isn’t just about how much time has passed. It’s a testament to the hard work and dedication of generations of Winair employees, the unwavering loyalty of our passengers, and the trust our regional and international partners have placed in us for decades.”
van de Velde added that the airline is equally proud of its longstanding role in supporting economic progress across St. Maarten and its neighboring islands. “As we mark 65 years of connecting the Caribbean, we remain focused on investing in our future while continuing to deliver the reliable, high-quality service our customers have come to count on from us,” he said.
The unveiling of the commemorative aircraft is just the first of dozens of anniversary initiatives planned throughout the year. Passengers and community members can expect a full calendar of celebrations, limited-time promotional campaigns, local community engagement activities, and industry events that highlight Winair’s outsized contribution to Caribbean aviation over the past 65 years.
Looking ahead, the carrier enters its anniversary year with confidence, outlining ongoing investments in expanding its route network, upgrading its fleet, enhancing the customer travel experience, and rolling out innovative service offerings that make regional travel across the Caribbean more accessible and convenient than ever before.
The launch of the first commemorative aircraft formalizes the start of Winair’s anniversary celebration: a moment that honors the carrier’s foundational legacy, celebrates its present-day role as a regional aviation leader, and reaffirms its commitment to powering the future of connected travel across the Caribbean.
Founded in 1961, Winair is the oldest continuously operating regional carrier in the Caribbean. It currently serves 17 island destinations from its St. Maarten hub, with a core mission focused on safe, reliable, on-time service that links people, businesses and communities across the region.