Originally Posted by bbtrvl

Yes you will have to fill out an OFAC declaration when flying between the US and Cuba. Even if you are not "persons subject to US jurisdiction" (US citizens and green card holders, etc) you're still within the US and traveling on US flag carrier and therefore subject to the embargo.

So for example, you cannot travel from the US to Cuba as a tourist, regardless of your citizenship.

There may be even more problems with your plan. You may not be able to book a ticket originating in Cuba to the US, and you may be required to book round-trip originating from the US.

You might look at Canada. Toronto is not that far from NY.