Cuba travel trump changes

Do not over think this,most likely nothing will happen, you being questioned in any serious way.

Which OFAC category are you intending to choose ?

I have seen nothing official about the date of the new regulations and a number have suggested that there should be a period from publication to when they come in to force.

If we can travel under the old regulations then 'General license for people-to-people travel' otherwise we would need to choose one of the others so 'support for the Cuban people' would be the closest one but that states - 'the schedule of activities does not include free time or recreation in excess of that consistent with a full time schedule'. We are not planning to have such a full time schedule.

"People to people" also requires that "Each traveler has a full-time schedule of educational exchange activities that will result in meaningful interaction between the traveler and individuals in Cuba;".

So it does. But that's generally the one people have been choosing if going there as tourists. And that's the one that Trump plans to remove.

September 15 was supposedly the 'deadline' for announcement of new rules (90 days after Trump's announcement), so who knows what's going on now, or if they will even announce new changes at all. I thought the Cuba diplomat stuff making the news rounds last week was going to presage an announcement of restrictions of some sort, as a way to say "hey this is why we're doing it!!! Cuba = bad", but then nothing came of that and it's been a full week since the diplomat stuff made front page news (again) with no announcements other than Rex Tillerson saying "maybe we'll do something, I dunno."

I don't know at all if this is binding, but we already printed out the affadavits and signed them. You are probably on Air Alaska? https://www.alaskaair.com/~/media/Files/PDF/QT-07-Cuba-Affidavit.pdf

No idea if it's legally meaningful at all of course, but we printed and signed them while the current rules were still in effect so maybe that will count for something. We bought our tickets in August. I bought travel insurance before the June 16 deadline, with Cuba in mind, but I don't know if that would actually count since it's not like the insurance is Cuba-specific.

I could not find anything so much about "what happens if you planned things between June 16 and [whenever new OFAC regulations are actually announced]", except Marco Rubio's June 16 tweet saying that AirBnB is fine for individual travel under the Support for the Cuban people category, which seems like it will be left alone: https://twitter.com/marcorubio/status/875666795763511296?lang=en (his tweet was after Trump's announcement).

If you're flying to and from Cuba from and into the US you will need to sign the affidavit until further notice ,it's kept on file with the airline and not the US government.

September 15 was supposedly the 'deadline' for announcement of new rules (90 days after Trump's announcement),

Supposed by whom ? I have not seen anything from official sources about the dates. They had 30 days to start work - but then ? I suspect that the 90 days was the invention of a blogger / commentator.

As you say - the changes may never appear. They have done a lot of their work already and scared off a lot of independent travellers and given those selling high-priced group travel grounds to lie to people that groups are the only way to go.

If you bypass the USA both to and from Cuba, you will avoid all the OFAC cold war problems with travel to Cuba. You do not have to fly in and out of Cuba from the USA!