The simple, undeniable fact (the one you keep skirting) is that you and your entire group is planning on pumping American money into Cuba's economy. Also known as Castro's economy.
Go. Be well. Have a Rum Runner on the beach.
But don't dance around the fact that you *are* supporting Castro. That is a fact, as sure as you would be supporting Chirac with a trip to Euro-Disney. You soak up some culture, Castro (and his regime) are soaking up your American cash.
There are *many* other countries that would gladly accept your tourist dollar.Free countries. It may be your money, but there is also a very real principle that you are ignoring. I cannot define the line between 'goodwill ambassador' and 'communist enabler'. Can you?