Your best bet is leave from Canada. Americans have secritly done this for decades. Perhaps, if you could get an airline that stops in the USA prior to traveling on to Cuba you may do this. Personally, I would travel elsewhere in South America for less money.
PS If you must go to Cuba you may find an American tour operator to be your best bet. Do to Trump making it harder for US citizens, I would think you will find a flight to Cuba from the US not very abundant. 11 days agoAnswered by Anonymous via WorldNomads.com
Not sure about new regulation, but I went in Sept 2016 from NY to Havana, wasn't an issue the plane just stopped at the caymans so that it wasn't a direct flight. You get your passport stamped at the stopover point (for e.g. my friend went through Cancun) so that you enter/exit the US from that country rather than Cuba. If nothings changed it should be the same for returning. 11 days ago
There are flights from Cuba to the USA, check with Jet Blue, Delta and a few others . . . Better yet, check with a travel agent since there may be some questions about your documentation also. 1 day agoAnswered by Ester Herz via WorldNomads.com