We went as tourists 'illegally' about 3 years ago to Cuba via a trip listed on tripcentral.ca.

It was a charter from Toronto. Had a wonderful time and loved the Cuban people, who are smart, funny and know exactly how they are being oppressed by the embargo and their government. By the way, the embargo is used regularly by the government as an externalized blame for their sad state. When we lift it, they will have no excuses and I predict a quick demise of their sclerotic system.

In any event, when returning to Toronto I asked the Canada immigration to not note where we had been. He said with a smile that the US shares the system with them and not to worry. When clearing US immigration in Toronto for my Seattle flight, I said I was in Cuba. He said welcome home. End of story.

Reminds me of another Cuba story by a man I know. In this case he had been skiing at Whistler. He is a very honest man. While in Canada he bought some Cuban cigars. Upon driving back to the US he was asked if he has anything to declare. He declared his Cuban cigars. Upon hearing this, the customs agent looked at him sternly and said "You know those are illegal in the US. So what I need you to do is take them home and burn them....slowly".