Over its 65-year history, Winair has experienced extraordinary change. Photo: Winair

The evening was both a celebration of Winair's journey and a heartfelt thank-you to the people and partnerships that have helped shape the airline since its founding in 1961.

Guests gathered to reflect on Winair's remarkable history, recognise the pioneers who laid its foundation and celebrate the employees, partners and stakeholders who continue to carry the airline forward today.

Honouring the Vision that started it all

Winair's story began in St. Maarten on August 24, 1961, when pioneering aviators Georges Émilien Gréaux and Hippolyte "Faustin" Lédée joined forces with St. Maarten businessman Norman "Chester" Wathey.

Their shared vision was simple but ambitious: to create reliable island-to-island air transportation for the people of the Caribbean.

That vision quickly took flight. In 1963, Winair inaugurated regular service to Saba, becoming the first airline to provide scheduled service to the island. In 1965, the now-iconic Twin Otter joined the fleet, an aircraft that would become inseparable from Winair's identity and uniquely suited to some of the Caribbean's most challenging and extraordinary airports.

As part of the anniversary celebration, Winair paid special tribute to the Wathey, Lédée and Gréaux families, recognising the vision, courage and entrepreneurial spirit of the founders and the lasting legacy their families represent within the Winair story.

Celebrating 65 years together

The official programme featured remarks by Winair CEO Hans van de Velde, Minister of Tourism, Economic Affairs, Transport and Telecommunication Grisha Heyliger, Prime Minister Dr Luc Mercelina, and President of Parliament Sarah Wescot-Williams.

Their remarks reflected not only on Winair's longevity, but also on the airline's importance to St. Maarten and the wider 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."

A Caribbean story of Resilience

Over its 65-year history, Winair has experienced extraordinary change.

The airline expanded its network, introduced new aircraft and developed partnerships that strengthened regional and international connectivity. It also faced some of the most challenging periods in Caribbean aviation, from changing economic conditions and devastating hurricanes to the unprecedented impact of the COVID-19 pandemic.

Following Hurricanes Irma and Maria in 2017, Winair resumed service to most of its destinations within just eight weeks. During the pandemic, the airline once again demonstrated its resilience, navigating one of the most difficult periods in aviation history and emerging ready to rebuild and grow.

Today, Winair operates more than 25,000 flights annually and carries over 330,000 passengers each year, with a fleet that includes its iconic Twin Otters alongside ATR 42 aircraft.

Yet despite how much has changed, the purpose at the heart of Winair has remained remarkably consistent: providing safe and reliable connections between Caribbean communities.

More Than an Anniversary

The 65th Anniversary Celebration was intentionally centred around Winair's stakeholders.

Partners and guests from across the Caribbean and internationally came together in St. Maarten for an evening of recognition, conversation and celebration. It provided an opportunity to strengthen long-standing relationships, create new connections and recognise the many organisations and individuals who have contributed to Winair's success.

The evening also celebrated the generations of Winair employees who have kept the airline flying for 65 years—from pilots and cabin crew to maintenance, operations, customer service and the many teams working behind the scenes.

The journey continues

Sixty-five years after three pioneers envisioned a better way to connect the islands, their idea continues to fly.

The aircraft have changed. The network has grown. Generations of passengers and employees have come through Winair's doors.

But the connection remains

As Winair celebrated its past, the evening was equally about looking toward the future: strengthening regional connectivity, continuing to invest in its people and operations, and building on the partnerships that will carry the airline into its next chapter.

65 years. Countless journeys. One Caribbean.

Thank you for being part of our journey.