If I was sailing to Cuba I wouldn't start from there.
But then I'm Australian.
You could try taking out Canadian citizenship.
I am a Canadian and I would love to do Cuba, My kids are wanting to go there as well, it is their first choice for travel. I think the people of Cuba are great, I have contacted many them often, I know Canadians who live there and just love it. There are charters going from Canada hourly to holiday there, and they all love it. Canadians are not a hated people, our government is open minded, and they seem to tell us the truth, or at least someone will tell us the truth and it will not be considered an act of treason. The dictatorship to the south has a few issues to be resolved. Treating their people better, not creating fights with neighbours, and not being so dam defensive about every little thing ...but I guess when they stick their nose into the affairs of others ...they fight back and hate you.
It is not the US citizens who are at fault, it is the governments that gets into power ..with lies and deception. It is time for the US Citizens to take charge of the control of the country, and create a place worth living in. As it stands now, the US is not the land of the free ...many other countries are the "land of the free", the US is probably about #20 on the list, perhaps more like #30.