I've never seen a Checker Marathon in Cuba. That's probably because the Marathon, built in Kalamazoo, Mich., didn't go on sale until September 1961, more than a year after the direct export of U.S. vehicles to Cuba ended.
But the Marathon's 1950s styling makes it look like a Cuban cab, at least to the Toronto residents who hopped into the Checker that Transat Holidays put on the streets of the Canadian city to promote its winter sun excursions. And the actors playing the driver and his friends are certainly convincing.
The video makes me think of an earlier commercial that just might have been the inspiration for the Transat campaign. See The Lost Chevy Commercial.