Since the thawing of tensions between Cuba and the US, the desire to travel has peaked and airlines have begun offering flights to the island. (see attached link for direct flight list: http://cubajournal.co/here-are-all-direct-flights-to-cuba-from-the-u-s-in-2016/)
However, there is still a lot of confusion as to who can go, because technically traveling there is still prohibited. Visas are granted if you fall under one of 12 specific categories which can be found at https://www.ecfr.gov/cgi-bin/text-idx?SID=b5ee59d94ee45bba6a049240298f1cff&mc=true&node=se31.3.515_1560&rgn=div8
It was easy for me to declare ‘journalism’, but you’ll have to decide what is best for you.
In June 2017, President Trump made a change prohibiting people-to-people activities, which could be declared if you were to tour Cuba through an organized group (I did have one friend declare this and traveled privately on her own itinerary). That regulation technically went into effect July 2017, but at the time of booking my flight (Aug 4th) there was still an option to declare people-to-people visas.
Upon booking your flight you’ll be asked to declare your reason for travel and upon completion you’ll be emailed all the necessary travel information.
I booked my flight from Ft. Lauderdale and since I recently started walking after breaking my foot, I requested wheelchair assistance. Whether that made a difference in my experience or not is unclear. After a routine security check we were wheeled to our gate, simple as that! We didn’t sign an affidavit; we weren’t even stamped out of the country! It was as easy as any domestic flight, except the end destination was Cuba.
Upon return we were handed the typical customs forms as we boarded and declared our souvenirs (cigars and rum). Again, I had wheelchair assistance and we rolled right through customs with no issues, no questions asked, right into the U.S.A.