I agree with Calchas, you should definitely be careful. I live in the U.S. (visitor visa), have a European passport and just came back from Cuba. I was pretty concerned about this as well, so here my experience: Flying to Cuba was not a problem at all, you just need to buy a visa. Also, I had no problems when coming back to the U.S. at all (the officer at customs only asked me what I did in the U.S.), BUT you should bear in mind that non-U.S. citizens entering the U.S. are almost always asked at customs 1) what they’re doing in the U.S. and 2) what they were doing abroad (if they live here), meaning that you have to be prepared to answer the latter question without mentioning anything that might be considered as tourism in Cuba.
I didn’t want to risk anything, so I had my travel agency prepare me a complete schedule of my trip to Cuba, which stressed activities considered as educational and people-to-people interaction (always accompanied by a local guide). No mentions of anything that may be considered as tourism.
I would recommend always to book your trip with a U.S. travel agency, as they are familiar with all the regulations and work with licensed Cuban agencies. They will give you a schedule that you can present at U.S. customs and the visa you need to enter Cuba.
I hope this helps!
Legally speaking, you are not permitted to travel to Cuba from the United States for touristic purposes. The regulations bind “persons subject to US jurisdiction” which includes most people who happen to be in the United States, regardless of their citizenship, as well as US citizens wherever they are. As you will be in the United States at the time of departure, that includes you.
Although you are very unlikely to be examined on the outbound journey, you could be denied entry on your return to the United States if during your entry examination this fact comes to light.
In principle if you were to book two separate flights, one to Mexico City and an onward one to Havana, on separate tickets, and making the booking while outside the United States, it seems to me you would not be in violation of the order. (Providing you are not otherwise subject to US jurisdiction.)
Given the present climate, I would be cautious in attempting to circumvent this ban by misrepresenting your activities in Cuba, but that is a risk for the reader to weigh.
See also the following Treasury advice: https://www.treasury.gov/resource-center/sanctions/Programs/Documents/guidance_cuba_travel.pdf
There are several direct flights from USA cities to Havana (I just checked a few minutes ago) and there are flights available. Things have not changed under the Trump administration, as yet.
To travel you need a Tourist card. The information for a UK citizen visiting Cuba is found here:
https://www.gov.uk/foreign-travel-advice/cuba/entry-requirements
There is no indication you would have problems returning to the USA just from the travel, so far as you don’t bring items from there which could be seen as trading with Cuba.
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