After denying that I worked for the U.S. government, the official began a volley of questions:
Cuban Official: Why are you in Nueva Gerona?
Me: I am an aviation enthusiast and wanted to fly Cubana.
Cuban Official: But why are you not staying?
Me: Because I fly out of Havana this afternoon.
Cuban Official: Where will you go?
Me: Costa Rica, then Los Angeles.
Cuban Official: So you just want to fly? You are not working for the Americans or in the U.S. military?
Me: Correct. I was hoping to fly on the AN-24, but sadly they said it was broken today.
Cuban Official: How long are you in Cuba?
Me: Two days
Cuban Official: Why only two days?
Me: Because that is all the time I have. I would like to stay longer.
And thankfully, that was it. The official looked at my passport picture page a few more seconds, handed me back my passport, and motioned for the airport security staff to let me through to the screening area.
Boarding had already begun and the FA was surprised to see me back. Guess who my seatmate was?
Yes, the government agent.
He had the window, I had the aisle. We exchanged no more words.
I did exchange words with a Cubana pilot across the aisle from me who asked me how I liked Cuba and said that he was flying to Paris later that day.
We took off, service was identical to the outbound, and we landed on time in Havana. I was not followed off the plane and found myself in a dilapidated baggage claim area.
Through the exit, I found myself outside with the morning air still somewhat cool. I still had several hours before my flight back and I was not going to just sit at the airport.
It was quite a risk to even attempt a same-day return with no tickets on sold-out flights, but it all worked out. I missed on the AN-24, could have been arrested if the agent did not buy my story, but looking back I have to smile upon what had transpired. And it was only 10am.
Read more of my Cuba trip report:
Planning a Trip to Cuba
Los Angeles to Havana in TACA Economy Class
Visa Requirements for Visiting Cuba
Day One in Cuba: A Tour of Havana
Day One in Cuba: An Evening Surprise
Day Two in Cuba: Accused of Being An American Spy!
Day Two in Cuba: Escorted Flying
Day Two in Cuba: The Juxtaposition of Two Cubans
Havana to Los Angeles in TACA Economy Class
10 Tips for Visiting Cuba
Why You Should Visit Cuba Now