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Curious if anyone has flown to Cuba or overflown Cuba VFR? What's the process like? I was recently in Key West and thought it would be neat to continue south another 90 miles to Havanah, but hypothetically given I've never made the flight. I've heard some pilots say it's very difficult or impossible, but unsure why. I thought US relations with Cuba were better since Obama?

I figure the relations with Cuba have definitely changed since President Obama’s administration. Be ready and aware of permit required to fly into their airspace and possibly additional charges for airspace usage.

I myself have not flown into Cuba but do remember getting over flight permit to go to Cayman Islands.

I would suggest a handler that’s knowledgeable about Cuba operations if you have never flight planed there before.

Logan, yes, with two best buds we flew my DA40 to Cuba in March 2016... here's a summary video:

I'm not current on the limitations the US Treasury may or may not have for GA travel, so you'll have to check that out yourself. All I can say is that in 2016 this was a very doable trip... and a wonderful adventure!!

Let me know if you have any questions.
Wayne