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Americans traveling to Cuba

I’m sitting here telling one of my co- workers about our trip to Santa Maria last week. He has said in the past he would like to visit with his wife. However, his wife is an American citizen, never having applied for Canadian citizenship.
I know it is common for US citizens to fly through Canada or Mexico to Cuba. Is it true the Cuban immigration officials will not stamp a passport if asked?
I’m also hearing rumors the US government is going to start wanting manifests of all on board passengers for flights entering US air space. Does anyone know when this is coming down and how will it effect US citizens flying out of Toronto to Cuba?

I believe the US have been getting passenger manifests for several years already.

The policy will ‘officially’ be implemented next year, although many believe that it is already ‘unofficially’ carried out. There was an article about it in this week’s news:
http://thechronicleherald.ca/Search/1092206.html

Perhaps they were already getting the names and the new policy is meant to add gender and date of birth?!

She’s a America living in Canada? The short answer is simple: Cuban travel holds zero issues for her because she never interacts with American Immigration. (And no, Cuba does not stamp any Passports, American or otherwise.)

The Passenger Manifests are a dead issue too. OFAC (Office of Foreign Assets Control) has never once prosecuted an American tourist traveling illegal to Cuba on the basis of a passenger list. Not only that, their funding from Congress has dried up completely and now they aren’t processing any cases against tourists without a confession and hard physical evidence.

In other words, it’s perfectly save for her to travel to Cuba.