The law I'm not advocating breaking the law, but I've read something like 60,000 Americans visit Cuba, every year. Being prosecuted is almost unheard of, it seems; but, bringing back goods purchased there, using your credit card or debit card, making ATM withdrawals, or declaring in any manner you'd been there, including on the arrival form when returning to the U.S. would force U.S. Customs/Immigration to launch an investigation. Mexico represents a good point of embarkation for a trip to Cuba, for those who choose to go, with RT airfares as little as $250 US. A day trip would not be practical, I would think, given the time it takes to clear airports, coming and going, even if you could find an early departure and a late hour return.
A couple more points: If you have an American bank issued bank or credit card, they will most certainly not work in Cuba. If you have a foreign bank card, you have to make sure there is no American affiliation, as the card could possibly not work at all. For example, the bank could be in Europe, but the credit/bank card clearing house is in America, then the card won’t work. If any American goes, they have to exchange the money, etc. This reinforces the law that states Americans can not spend money in Cuba. Also, when President Obama came into office, one of the first things he did was change the laws to allow family members to visit their families in Cuba, but that is only 1 time a year. This was never allowed prior to President Obama, so if you were a Cuban American, who had family members in Cuba, you were SOL. From what I have heard on the news and stuff, you have to do special paperwork, etc to do this. And I’m not quite sure how airlines handle this, as up until last year, no American flights were going to Cuba. I’m sure a simple google search can provide more details on this. Perhaps check the US State Department………… Its still all a pity to me. I merely would love to go see the country as a tourist to see what its like. That goes for any foreign country. As a tourist, you want to see what else is out there, so to speak.
V is right. So many Americans are able to vacation there. If you travel through Mexico to get there, spend cash only, and don't bring back any obviously Cuban souvenirs, there's no reason for them to suspect. Also, when you go through customs in Cuba, they won't stamp your passport if you're American. I think they give you a separate piece of paper with a stamp. I understand Cubans are generally very welcoming of American tourists. (So it's pretty much just the USA that holds a grudge... not surprised haha) I haven't been to Cuba myself, but I did look into it a few months ago and it actually seems pretty easy to do.
I know Americans that have been to Cuba recently and this is how they did it. It is only Uncle Sam that has the problem with it. Not Cuba.