Do I qualify to travel UK > Cuba via Miami as a non US citizen under the ‘family member’ general licence category?

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Answering my own question:

The answer to this question Travel from the US to Cancun with a layover in Cuba as an European citizen is correct. The restrictions apply not only to citizens and residents but to anyone within the US.

A non-US citizen fiancé / fiancée is not eligible to travel directly between the US and Cuba to visit their partner because the OFAC regulations and conditions §515.561 pertaining to the ‘family visit’ general licence category restrict it to close family members.

‘Close family members’ is defined in §515.339 of the OFAC regulations as related by blood, marriage, or adoption and who is no more than three generations removed. Therefore a fiancé or fiancée (or any other person who is not a close relative) cannot legally self-certify a family visit when booking or checking in for a flight.

In conversation with a member of the American Airlines service team it was also mentioned that the Cuban authorities may ask to see proof of the family relationship on arrival in Cuba.

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