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I'm hoping to visit Cuba for a few days during my trip to the US. I'll be staying in Tampa, so a direct flight to Havana is possible, and probably the cheapest option. I've read about the travel restriction if you leave from the US, and how they have changed earlier this year. I will try to find a way to travel under the "support-for-the-Cuban-people" category.

I'd like to hear from non-US citizens who have travelled successfully to Cuba from the US since July 2019.

What is an example of an acceptable itinerary? I'd like to stay at a casa particular, which falls into that category, but I'm unsure of other activities. I'm going to plan this myself and not use a travel company.

Also, as a non-US citizen, what process will I go through at the border when I leave, and when I return? Do I need to provide an itinerary when I leave (and how much detail does it need), and do I need to provide proof of my activities when I return (and what should I show)?

What kind of consequences are there if on my return to the US if I don't have enough supporting evidence?

  • Have you considered departing from Mexico? Most of my friends go to Cuba via Mexico City. – AussieJoe Nov 6 '19 at 15:45
  • I have, but the direct way is much more affordable for me – Phill Nov 6 '19 at 23:06
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I've since been and returned on my trip to Cuba departing from the US.

On my outbound journey, I was asked at the check in desk what the purpose of my travel was. I replied "support for the Cuban people" and that was it, I was allowed to travel.

On my return entry to the US, I was asked the usual entry questions (why are you here, when are you leaving), and I was allowed to re-enter.

Hence, from my experience, the actual leaving and entering is unlikely to require discussion of your travel itinerary. Of course this could be dependent on the check in staff or border control officer you encounter.

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Staying at a casa particular in and of itself doesn’t qualify as support for the Cuban people, as defined in §515.574 of the regulations https://www.ecfr.gov/cgi-bin/retrieveECFR?gp=&&mc=true&n=sp31.3.515.e&r=SUBPART&ty=HTML#se31.3.515_1561

(a) General license. The travel-related transactions set forth in §515.560(c) and other transactions that are intended to provide support for the Cuban people are authorized, provided that:

(1) The activities are of:

(i) Recognized human rights organizations;

(ii) Independent organizations designed to promote a rapid, peaceful transition to democracy; or

(iii) Individuals and non-governmental organizations that promote independent activity intended to strengthen civil society in Cuba; and

(2) Each traveler engages in a full-time schedule of activities that:

(i) Enhance contact with the Cuban people, support civil society in Cuba, or promote the Cuban people's independence from Cuban authorities; and

(ii) Result in meaningful interaction with individuals in Cuba.

(3) The traveler's schedule of activities does not include free time or recreation in excess of that consistent with a full-time schedule

I was told recently by an American Airlines representative that travellers are required to provide proof at check-in in the US that they qualify to travel under one of the general licence categories. Record-keeping and penalties for violating OFAC regulations relating to Cuba are published here https://www.ecfr.gov/cgi-bin/retrieveECFR?gp=&SID=&mc=true&r=PART&n=pt31.3.501#se31.3.501_1701

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