Winair and Contour Airlines Launch New Interline Partnership Connecting San Juan, Puerto Rico, St. Thomas, the U.S. Virgin Islands, and Dominica to Strengthen Caribbean Connectivity and Boost Regional Travel Across the Islands

There’s a new way to connect through St. Maarten.

Winair has launched a new interline partnership with U.S.-based Contour Airlines, a deal that took effect last month and opens up a fresh set of seamless itineraries across the Caribbean.

The agreement means Contour Airlines can now sell tickets that include Winair-operated flights, letting its customers book straight through to destinations across the region on a single itinerary. The biggest headline for passengers: travelers across Winair‘s network will now have improved access to San Juan, Puerto Rico, routed through St. Maarten, with those bookings available directly through Contour Airlines.

It’s one of several similar agreements Contour has signed in recent months as it grows its Caribbean footprint.

It’s a deal that further cements St. Maarten‘s growing role as a regional connecting hub, linking visitors to destinations throughout the Caribbean through a single carrier relationship.

“This partnership represents another important milestone in expanding our network reach,” said Winair CEO Hans van de Velde. “By collaborating with Contour Airlines, we are making it easier for travelers to connect through St. Maarten and explore more destinations within our region.”

For Contour, the agreement is the latest move in what has been a remarkably fast Caribbean buildout. The Tennessee-based carrier only launched its first regional flights in late summer of 2025, kicking off with service from both San Juan and St. Thomas to Dominica — routes that gave the island its only nonstop jet links to Puerto Rico and the U.S. Virgin Islands. From there, the airline added flights between San Juan and Princess Juliana International Airport in St. Maarten, a route now operating three times per week on its 30-seat jets. Contour now serves more than 30 destinations across the United States and the Caribbean, and earlier this year struck an interline deal with JetBlue that opened up that carrier’s network of more than 100 destinations to its passengers.

It’s a clip that reflects how bullish the airline is on the region. “We see a lot of opportunity in the Caribbean,” Contour CEO Matt Chaifetz said earlier this year.

“We are excited for our new partnership with Winair,” said Ben Munson, President of Contour Airlines. “Contour passengers will now have the ability to connect onto Winair’s impressive network beyond St. Maarten throughout the Caribbean.”

The new Winair tie-up adds another layer of onward connectivity to that growing footprint, giving Contour customers a gateway into the dozens of regional routes operated by Winair.

It’s the latest in a string of interline deals aimed at widening the carrier’s connectivity across the region and reinforcing St. Maarten as a launchpad for Caribbean travel.