WINAIR: Connecting the Caribbean Islands Since 1961
What if your next Caribbean adventure began the moment you took off? Since 1961, WINAIR has been connecting travelers to some of the region’s most captivating islands, making island hopping an essential part of the Caribbean experience. From the exclusive shores of St. Barts to the volcanic landscapes of Saba and the peaceful charm of St. Eustatius, this regional airline brings together extraordinary destinations, cultural discoveries, and memorable escapes.
History & Identity — A Caribbean Aviation Legacy Since 1961
Founded in 1961, Windward Islands Airways International N.V., widely known as WINAIR, has played an important role in connecting Caribbean islands for more than six decades.
Originally focused on providing air transportation between Sint Maarten, Saba, and St. Eustatius, the airline gradually expanded its operations to serve a growing network of Caribbean destinations.
Headquartered at Princess Juliana International Airport (SXM), in Simpson Bay, WINAIR has built its identity around an in-depth understanding of regional aviation and the unique geographical characteristics of the islands it serves.
Its development reflects the importance of reliable regional connections in an archipelago where neighboring territories may have very different airport facilities, economic activities, and travel requirements.
Beyond leisure travel, WINAIR helps maintain connections between Caribbean communities, supports regional business activity, and provides transportation options for residents and international visitors.
Today, the airline continues to combine its Caribbean heritage with an expanding approach to regional mobility, offering scheduled services and private charter opportunities for travelers looking to experience the islands in different ways.
Destinations & Connections — Discover the Caribbean from St. Maarten
With its main hub at Princess Juliana International Airport, WINAIR provides access to an extensive selection of Caribbean destinations. Among its most distinctive routes are the connections to St. Barts, Saba, and St. Eustatius, three islands that offer remarkably different travel experiences.
St. Barts represents one of the Caribbean’s most exclusive destinations. Known for its beautiful beaches, private villas, prestigious hotels, and refined French island lifestyle, Saint Barthélemy attracts visitors seeking sophisticated yet relaxed luxury. WINAIR provides flights to Rémy-de-Haenen Airport (SBH), making it possible to continue a Caribbean getaway after arriving in Sint Maarten.
Saba offers a completely different environment. Nicknamed “The Unspoiled Queen,” the island is celebrated for its volcanic scenery, tropical vegetation, dramatic landscapes, and hiking opportunities. Dominated by Mount Scenery, it appeals to nature lovers seeking a peaceful and authentic Caribbean escape.
St. Eustatius, commonly known as Statia, is another fascinating destination. Its historical heritage, volcanic landscape, and understated atmosphere invite travelers to discover a less-traveled side of the Caribbean, where cultural exploration and natural beauty take center stage.
WINAIR’s network also includes Antigua, St. Kitts, Nevis, Tortola, Dominica, Montserrat, St. Lucia, St. Vincent, Aruba, Curaçao, Bonaire, Barbados, and Trinidad. Flight frequencies and available connections depend on the route and operating schedule.
Caribbean Island Hopping — One Journey, Multiple Experiences
One of the greatest privileges of traveling in the Caribbean is the opportunity to experience several islands within a single vacation. Each destination has its own landscapes, cultural heritage, culinary traditions, and atmosphere.
With WINAIR, travelers can create itineraries that combine the cosmopolitan energy of St. Maarten, the understated sophistication of St. Barts, the volcanic wilderness of Saba, and the historical charm of St. Eustatius.
For international visitors staying in luxury villas, boutique hotels, or beachfront resorts, regional flights provide an opportunity to expand their Caribbean journey beyond a single island.
This flexibility also makes WINAIR an important transportation option for local residents and business travelers who need to move between neighboring Caribbean destinations.
Fleet & Expertise — Aviation Designed for the Caribbean
Flying between Caribbean islands requires specialized operational knowledge. From short airport runways to different terrain conditions, regional aviation presents challenges that demand appropriately selected aircraft and experienced flight operations.
WINAIR operates a fleet that includes the De Havilland Twin Otter, a 19-passenger turboprop aircraft known for its short takeoff and landing capabilities. Its design makes it particularly suitable for certain smaller island airports.
The airline also operates ATR 42-500 regional aircraft, configured for 48 passengers, which support connections across a broader selection of Caribbean destinations.
Together, these aircraft types allow WINAIR to adapt its operations to the particular requirements of different routes and airports.
In September 2026, WINAIR announced that it had achieved both IOSA and ISSA registration under IATA’s operational safety assessment programs, covering its ATR 42 and Twin Otter operations respectively. The milestone reflects the airline’s continued focus on operational standards.
Private Charters — Personalized Flights Across the Caribbean
Beyond scheduled flights, WINAIR offers private charter services throughout the northeastern Caribbean, providing an additional option for travelers with specific transportation requirements.
Whether arranging a business journey, group transfer, private event, or personalized island itinerary, guests can submit a charter request based on their destination, preferred schedule, and number of passengers.
For travelers staying in exclusive villas and luxury hotels in St. Maarten or St. Barts, private charters offer an opportunity to explore customized travel arrangements, subject to aircraft availability and operational requirements.
Travel Experience — Planning Your Caribbean Journey
WINAIR provides a selection of services designed to help passengers organize their journeys, including online reservations, booking management, check-in options, baggage services, and assistance for travelers with specific requirements.
Online check-in is available starting 24 hours before departure, subject to booking conditions. The airline generally recommends arriving at least 90 minutes before a scheduled flight and advises passengers departing from Sint Maarten between 1:00 PM and 6:00 PM to arrive at least three hours early because of potential airport congestion.
Passengers should also verify passport requirements, travel documentation, visa rules, and baggage allowances for each destination. When connecting between separately booked airlines, collecting baggage and completing a new check-in may be necessary.
These practical considerations are particularly important for travelers planning a multi-island itinerary, where local entry requirements and connecting flight arrangements can vary from one destination to another.
Highlights
- Caribbean regional airline founded in 1961.
- Main hub at Princess Juliana International Airport.
- Scheduled connections to St. Barts, Saba, and St. Eustatius.
- Extensive Caribbean destination network.
- Fleet including Twin Otter and ATR 42-500 aircraft.
- Online booking and check-in services.
- Additional passenger assistance and travel options.
- Private charter flights available upon request.
What Makes It Special
More than six decades of Caribbean aviation expertise, combined with a regional network that allows travelers to experience several remarkable islands during a single journey.
WINAIR ST. MAARTEN — Caribbean Flights, Island Hopping and Private Charters
For travelers searching for flights from St. Maarten to St. Barts, a regional airline connecting Caribbean islands, or convenient air transportation to Saba and St. Eustatius, WINAIR offers a long-established network of inter-island services.
Operating from Princess Juliana International Airport (SXM), in Simpson Bay, the airline connects travelers with destinations including St. Barthélemy (SBH), Saba (SAB), St. Eustatius (EUX), Antigua (ANU), St. Kitts (SKB), and Tortola (EIS).
Whether planning a luxury getaway to St. Barts, a nature-focused escape to Saba, a business trip across the Caribbean, or a personalized private charter departing from Sint Maarten, travelers can explore WINAIR’s schedules and available services.
Since 1961, WINAIR has been bringing Caribbean islands closer together, one flight and one unforgettable destination at a time.
Don’t Waste Another Minute >> WINAIR — Caribbean Airline & Private Charters
📍 Address:
Princess Juliana International Airport, Airport Road #99, Simpson Bay, Sint Maarten.
📞 Phone:
+1 721 545 4237
🕒 Opening Hours:
Sales office: Monday–Friday, 5:30 AM–6:00 PM.
Airport office: Daily, 5:30 AM–6:30 PM.
Call center: Daily, 8:00 AM–5:00 PM.
Reservations: Advance booking is recommended, especially during the high season for flights to St. Barts, Saba, and St. Eustatius. Private charters are available upon request.
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Princess Juliana International Airport, Airport Road #99, Simpson Bay, Sint Maarten
