One-way flights from Cuba to US - non US citizen

Hi all, I am planning to vist Cuba the next month, and I would love to stop in New York on my way back to Italy to visit some friends. I will therfore flight into Cuba from Italy, then fly from Cuba to NY one-way and then fly back to Italy from NY.
I was about to buy my tkt havana-NY on United's website (very convinient 3h direct flight), and got bogged down into the details of the policy to fly in and out Cuba from the US.
Do all these restrictions apply also for one way tickets FROM Cuba to the US? I am an Italian citizen.
Has anyone done something similar?
Many thanks in advance :)

In regard to eligibility, you must specify that you fall into one of the 12 OFAC categories for visiting Cuba,you may want to do that before next Friday's US-Cuba policy changes.

This is a requirement of the airline,I don't believe you can get around the requirement regardless of your citizenship since the US is involved in your travel itinerary.

The OFAC rules certainly apply to everyone flying from the US to Cuba, whatever their citizenship.

As YanquiBoy mentions, the airlines do seem to require you to make the same OFAC declaration when flying one-way from Cuba to the US. I don't know if that is an actual OFAC requirement - one of the airlines did indicate that it was a requirement placed on them as part of their license to fly those routes. But you should assume that you will have to make such a declaration.

I would advise you to keep an eye on what Trump says on Friday. Personally, I doubt that just booking before Friday will gain you much if the rules change.

Thank you both!
You are saying that the fact that I am not travelling from the US to Cuba but the other way around does not change anything - I still have to make the OFAC declaration. I was hoping to skip it to avoid getting asked about my trip. Do you thing I should simply stop worrying about it (since it s just a formality) or better to fly through another country?
I really just want to do the most convinient and easiest thing.
thanks again

Stop worrying about it,it's a minor formality, see your friends in NYC and see NYC with all of its wonderful cultures, including Italian.CIAO!

I should check with airlines flying to Habana(HAV) to Mexico(MEX or CUN) and then to New York(JFK or EWR). It is possible that it would cheaper. Also check ticket prices for Mexico City-New York-Italy. This way you avoid the USA/OFAC nonsense completely. Cuba does not date stamp your passport.

It may take more time, but if you are spending time in New York, it may not matter.

exactly! this was the answer I was looking for!
thanks so much :)

better to fly through another country?
I really just want to do the most convinient and easiest thing.

Understand that the "convenient and easiest thing" may go away as an option very soon.
Keep an eye on the news and check flights through Mexico or Canada.

Also flying through a 3rd country turns into an all day affair, I know ,I've done it many times. You must leave a lot of time between the 2nd and 3rd flight as you'll go through immigration and customs twice ,once through the 2nd country and once through the 3rd country.In Toronto you clear Canadian customs and immigration and then US customs and immigration which also happens to be stationed in the Canadian airport, international check in is at minimum 2 hours prior to departure which cuts it close when you think of the 3 or 4 lines you'll be standing on to get to the last leg of your trip. In Canada ,Canadian customs and immigration and US customs and immigration are located on almost opposite ends of the airport,so you're dragging luggage after Canada customs on your way to US customs and immigration .And for exactly those reasons are why I will never fly from a 3rd country again after flying direct from and to JFK.

Some places have it better organised. Flying Havana - Grand Cayman - Miami is pretty good, as Grand Cayman is a small airport and so you can get out and back in again fairly quickly.

How did you get on? I am about to do the same thing and have had all the same worries as you!

...third-country nationals, with a valid visa or other travel authorization issued by the U.S. government may be transported to the United States from Cuba;

https://www.ecfr.gov/cgi-bin/retrieveECFR?gp=&SID=ff1404f5ea556774a5b55e59a261c0a3&mc=true&n=pt31.3.515&r=PART&ty=HTML#se31.3.515_1572

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