Well, that says for travel “to, from and within Cuba,” so travel TO Cuba would mean, say, buying an airline ticket to fly there, which would mean you ned approval from the government.
But the website you link to does seem to indicate it’s not illegal to go there. I’ve always been told it was, but maybe that’s just been a misperception. I’d want to know for sure from the State Department before I tried to go, though.
Not an authority here, but I read an article about boaters going to Cuba, and the fact that it’s legal as long as they don’t spend money there. It was pointed out that most of them in fact purchase gasoline (at least), and therefore could be quite subject to scrutiny.
This brings up a very good question: Frank, would you be going to Cuba from the United States or from Canada?
If the latter–and IIRC, there are frequent nonstop flights to Havana out of a few Canadian airports–it would seem to me that you could leave your American passport/papers with Canadian friends or family in your departure city (you know enough CanaDopers, don’t you?), and travel out of a Canadian airport as a Canadian on his way to Cuba. I cannot see how you would be subject to US law if you travelled between Cuba and Canada on your Canadian passport.
If this information is useful, you can thank me with cigars when you get back to Canada. 
From scuba_bens link
I was a study abroad student in Lat. Am in the late 90s, Cuba was a not an uncommon spring break destination for other US students (who went without any US permission) As Vice has already side, my 2nd-hand impression was that you have to be pretty careless to get caught.
From Canada, certainly.
ScubaBen’s link certainly does seem to state that as a U.S. citizen, I am not allowed to spend U.S. dollars in Cuba. However, as it also states, “The basic goal of the sanctions is to isolate the Cuban government economically and deprive it of U.S. dollars,” I am still not certain that the restrictions apply to me travelling as a Canadian and spending Canadian dollars.
Well, as it doesn’t seem as if anyone can answer anymore certainly than I can, I’ll let the subject drop, and I won’t plan on touring in Cuba until (if ever) the U.S. gets over its phobia.
So does this mean I don’t get any cigars? Damn! I’m running low on Bolivar Coronas.
::d&r::
Though I’m not a cigar smoker, my understanding is that Cuban cigars are not what they used to be.
Perhaps I should start a new thread… 
The sanction applies to permanent residents, who we presume are always traveling with a non-US passport. So if you are traveling on your non-US passport, then I don’t see why you would have any more liberties from the embargo than a permenant resident. When you are enter a country on a Canadian passport, you are, after all, still a US citizen, regardless of whether or not your Cuban hosts know this fact.
IANAL, but it seems perfectly clear to me.
True enough, and why I am (reluctantly) coming around to the majority view.
Frank, I guess it mostly comes down to whether you think (or the US g’ment thinks) that you’re a person under their jurisdiction at the time of the trip.
Which is your natural born citizenship and which is your naturalized citizenship?
I’m an American citizen, with no other citizenships or residences or anything.
I traveled to Cuba in the mid-90s (and, for those who are going to get all picky about board rules, this was decades ago, and I’m not looking for advice on how to do anything illegal in the present or future).
My understanding is that, while it’s not illegal to travel to Cuba in and of itself, it is illegal to spend any money at all there (i.e., to engage in a transaction).
We went to Montreal first, and purchased tickets there for the flight to Cuba (and for the return flight, of course). We made our hotel reservations (in Varadero and in Havana) through a Canadian travel agency. The Canadians were more than happy to oblige. For them, going to Cuba is just a nice winter break. And we got a bunch of dollars to take with us, since we were aware that we wouldn’t be able to use our credit cards.
I don’t believe that the “CUC,” whatever that is, existed at the time. The only currency one could use in Cuba was the US dollar. In fact, I noticed that a popular tourist scam was for some enterprising Cuban to generously offer to exchange some hapless tourist’s dollars for Cuban pesos, which were (are?) absolutely useless. Nobody would take them.
Traveling around the country required a bit of hustle. The best way (sometimes the only way) to get from one town to another was to make unofficial deals with Cuban tour guides. For a few US dollars, you could ride their buses. Very handy, and much better than the buses Cubans had to use, which were unreliable and could involve hours of waiting around for the bus to show up.
Someone noted upthread that the Cuban authorities are aware of the situation for American travelers, and are cooperative, and won’t put a stamp in your passport. This was my experience. They stamped a card that was inserted into my passport. One the return trip, once we landed in Montreal, I threw it out.
Obviously I’m not encouraging you to do anything illegal. That said, I had a fantastic trip, and everyone I know who’s been to Cuba had a great time.
If you’re thinking of dancing on the head of a pin - how about bringing along a non-US companion and let them handle all the transactions for you?
That actually has been done. I’m aware of one family group that went from Canada where almost everyone was Canadian, but one of the kids was dual American-Canadian. So the kid wasn’t given any Cuban money and the adults in the group paid for any cash transactions for the kid, like food, souvenirs, etc.
Highly unlikely Uncle Sam will ever find out, but if the kid ever goes to the States when he’s an adult and is asked by US Customs, can truthfully say he’s never breached the embargo.
Of course, the OP’s question is hypothetical, as Frank is no longer with us.
RIP, Frank 
Here is what I was told. It is not so much that it is illegal to spend USD in Cuba, but it is illegal to spend any money, CAD, CHF, EUR in Cuba if the ultimate source of the money was the US. In my case, over 97% of my income is from Canadian sources and I assume that would make it legal for me to go there and spend money. I have never done it though.
Is the “spending money” thing still an issue with Americans?
Obama freed things up quite a bit and the most common way Americans visited Cuba was canceled by Trump in June. But that’s for travel. The money thing is still okay but of course you have to pay attention to Cuba’s two-currencies thing.
Uh, explain? Crossing fingers hoping for not sad news.
Gone since summer 2017