In Simpson Bay, St. Maarten, Windward Islands Airways International N.V. (Winair) marked a major milestone in August 2026: its 65th year of connecting communities across the Caribbean. The regional airline hosted a special stakeholder gala that brought together a cross-section of supporters, from local government leaders and aviation industry partners to tourism stakeholders, business executives, shareholders, long-time employees, and friends of the airline, to honor six and a half decades of service and partnership.
The event served a dual purpose: it celebrated the airline’s decades-long evolution while also extending sincere gratitude to every person and organization that have shaped Winair since its founding in 1961. Attendees gathered to reflect on the airline’s transformative history, honor the early pioneers who laid its foundational infrastructure, and recognize the current generation of workers, partners, and stakeholders that continue to drive the company forward today.
Winair’s origin story traces back to August 24, 1961, when two pioneering aviators, Georges Émilien Gréaux and Hippolyte “Faustin” Lédée, partnered with prominent St. Maarten businessman Norman “Chester” Wathey to turn a shared, ambitious vision into reality. Their goal was straightforward but game-changing for the region: to build a reliable air transportation network linking the scattered islands of the Caribbean.
That vision quickly gained momentum. Just two years after its founding, in 1963, Winair launched regularly scheduled service to Saba, becoming the first commercial airline to offer consistent scheduled flights to the small island. Two years later, in 1965, the airline added the now-famous De Havilland Canada DHC-6 Twin Otter to its fleet. The aircraft quickly became synonymous with Winair’s brand identity, perfectly engineered to navigate the short runways and challenging terrain that define many of the Caribbean’s small island airports.
As a centerpiece of the 65th anniversary celebration, Winair extended special recognition to the descendants of the Wathey, Lédée, and Gréaux families, honoring the founders’ vision, courage, and entrepreneurial spirit that remains a core part of the airline’s identity to this day.
The official anniversary program featured opening remarks from key industry and government leaders, including Winair CEO Hans van de Velde, St. Maarten’s Minister of Tourism, Economic Affairs, Transport and Telecommunication Grisha Heyliger, Prime Minister Dr. Luc Mercelina, and Parliament President Sarah Wescot-Williams. Each speaker highlighted not just Winair’s impressive 65-year run, but its outsize importance to the economic and social fabric of St. Maarten and the broader Caribbean region.
“For 65 years, Winair has connected more than destinations. We have connected families, communities, businesses and opportunities,” said Hans van de Velde, Chief Executive Officer of Winair. “Reaching this milestone is something we are extremely proud of, but we did not reach it alone. Our employees, passengers, shareholders, governments, airports, partners and stakeholders have all been part of this journey. This celebration was our opportunity to say thank you.”
Through 65 years of operation, Winair has navigated massive shifts across the aviation industry and the Caribbean region. The airline steadily expanded its route network, upgraded its fleet with modern aircraft, and forged strategic partnerships that strengthened both regional and global connectivity. It has also weathered some of the most severe crises the Caribbean has faced in modern history, from volatile economic cycles and devastating category 5 hurricanes to the unprecedented global collapse of aviation during the COVID-19 pandemic.
Winair’s resilience has been one of its defining characteristics. After the destructive landfall of Hurricanes Irma and Maria in 2017, the airline restored service to nearly all its destinations in just eight weeks, playing a critical role in the region’s recovery. During the COVID-19 pandemic, the company again demonstrated its ability to adapt, navigating one of the most turbulent periods in aviation history and emerging positioned to rebuild and grow its operations.
Today, Winair operates more than 25,000 commercial flights per year, carries over 330,000 passengers annually, and maintains a mixed fleet that includes its iconic Twin Otters alongside larger ATR 42 turboprop aircraft to serve growing passenger demand. Despite all the changes over six and a half decades, Winair’s core mission has remained unchanged: to deliver safe, reliable air connections between scattered Caribbean communities.
Unlike many corporate anniversary events that focus solely on organizational achievements, Winair’s 65th celebration centered the stakeholders that made its success possible. Partners and guests from across the Caribbean and around the globe gathered for an evening of recognition, relationship-building, and celebration. The event created space to strengthen long-standing partnerships, forge new industry connections, and honor the many organizations and individual contributors that have supported Winair through decades of change.
A key focus of the night was also honoring the generations of Winair employees that have kept the airline flying for 65 years, from frontline pilots and cabin crew to maintenance technicians, operations teams, customer service representatives, and the countless behind-the-scenes staff that keep operations running smoothly every day.
Sixty-five years after three pioneers launched a radical new vision for connecting the Caribbean islands, that original idea continues to thrive. Aircraft have been upgraded, the route network has expanded dramatically, and multiple generations of passengers and employees have passed through the airline’s doors. But the core purpose that launched Winair — connecting people across the Caribbean — remains the same.
While the celebration honored Winair’s rich history, it also served as a launch point for the company’s next chapter. Looking ahead, Winair plans to continue strengthening regional connectivity, investing in its workforce and infrastructure, and growing the strategic partnerships that will support its expansion for decades to come. As the airline’s milestone messaging puts it: 65 years. Countless journeys. One Caribbean.