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One of my friends had the opposite problem, language-wise! She learned much of her Spanish in Cuba, on study abroad, and now has to adapt when she goes elsewhere in Latin America. :D But she says it's helped her connect with Cuban ex-pats, who still immediately recognize her style of speech.
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There are heavy travel restrictions right now. No Americans are allowed. There are some exceptions: you can get a journalist visa. I went around the system and just flew in from Mexico instead. They don't stamp your passport and from the Cuban side, the more Americans that come the better. There is a chance of getting in trouble for this, but with close to 60K Americans going there every year, almost no one gets busted. You'd have to be extremely stupid (like telling customs on the way back into the States).
So basically what Uncle Sam doesn't know, can't hurt him. And Cuba is happy to oblige.
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you should stay in the "hotel presidente" (corner calz 7ma/Calle G) for a day or so - totally retro :)
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Great article and photos.