I wonder if it’s OK via Canada? Or Mexico? Jamaica? Do they mark up your passport? I know some countries give you a visa on a card you keep until you exit, then throw away, so the next country won’t bother you. It’s an open secret to keep trade going between “hostile” countries.
It is an open secret that many Americans go to Cuba but it is clear that they are breaking the law. Asking for advice here on how to best break the law is not a good idea and I bet the moderators will not like it.
A yatch club in Florida got into hot water with the feds for aiding (organizing) some boats that were going to Cuba legally!! http://www.havanacup.com/cd2.shtml
While we probably mostly agree their zeal is misplaced, the fact is they go after things like this as you can see.
Oh hell already, just go to Cuba!
It’s supposed to be a really cool trip.
I understand the Bahamas is another good place to catch a flight to Havana.
And yeah you can ask the customs officials not to stamp your passport. They’ll stamp another sheet and paper clip it in for you.
I was in Jamaica last year and there were a lot of people visiting Cuba. They have nice little 24 hour side trips you can schedule to visit there. You might want to contact one of the hotels there to get the best information.