Contour Airlines CEO: “We See a Lot of Opportunity in the Caribbean” 

By: - February 24th, 2026
dominica puerto rico
Dominica.

Tennessee-based Contour Airlines only began serving the Caribbean late last summer, but the carrier sees more potential for the region. 

Contour, which operates a flight of smaller regional jets, kicked off its regional network with flights from both San Juan, Puerto Rico and St Thomas, USVI to Dominica. 

The airline also has a new interline agreement with JetBlue.

In November, that network expanded with new flights from Puerto Rico to Princess Juliana International Airport in St Maarten. That route is now operating three times per week on Contour’s 30-seat jets. 

“We see a lot of opportunity in the Caribbean,” Contour CEO Matt Chaifetz said during this week’s CTO Air Connectivity Summit in Bermuda. “What we see as the opportunities are places where other airlines have struggled.” 

That includes other routes that don’t have any service where local governments are “willing to step in and mitigate risk and prove the market,” he said. 

“We haven’t built our entire business plan around the Caribbean, but we’re happy to deploy capacity there where it makes sense.” 

About the author

Alexander Britell is the founder and editor-in-chief of Caribbean Journal and one of the top experts on Caribbean travel worldwide, with decades of on-the-ground travel to the region and comprehensive knowledge of the entire Caribbean Basin.
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