We have always wanted to visit Havana. We finally decided to add it onto our Mexico trip this coming January. We'll be flying from Cancun International airport to Havana. As US citizens, we are slightly concerned about being questioned. I've read you can buy a $20 visa at the airport? I think we will fly Interjet. Do we buy the visas the check in counter?

Then we will fly back to the US (Fort Lauderdale) from Havana with Southwest. Will we be questioned at all coming back into the US? Anything we need to know? Is it pretty easy to just choose one of the 12 reasons for visiting Cuba? Or must there be more to it than that? How strict are they about your reason for visiting Cuba? Any documentation we will need to fill out?

Also, I read something about medical insurance being mandatory. And that it comes with your plane ticket. But is that only if you purchased a plane ticket from US to Havana? What if you are going Cancun - Havana - US?

Anything else I might need to know? Just want to be prepared and ready and not caught off guard by anything.

Forgive me, on a public forum you’re asking to prepare getting around laws?

Enjoy your time, but accept consequences if unlucky.

Our government has definite requirements when going to Cuba. Get those and make sure that you follow all of them. Don't do it until you have everything in order.