Most Americans don't know how easy it is to visit Cuba - and frankly, I am very glad. Cuba is an incredible place to visit and would only become less so with more traffic. Since only a *small* group of 'thought leaders' read Mattishness, I think it is safe to describe the process here.
Find a Canadian travel agent on the Internet - most any one will do. Call the agent on the phone and book a flight from Toronto or Vancouver (whichever is easiest) to Havana. Ask the travel agent to FedEx the paper tickets to you in the U.S. Then buy a separate ticket from your home to the Canadian departure city - match up the dates/times, etc.
When you land in Havana you may ask the passport stamper to stamp a loose piece of paper tucked in to your passport rather than the passport page itself. He may or may not oblige - but don't worry, it doesn't matter. The Cuban passport stamp is very small and illegible and does not say Cuba or anything else descriptive on it.
Go on and enjoy your trip.
When you return to the U.S. - tell the customs officer that you quite enjoyed your trip to Canada, thanks. As always when 'leaving a couple things out' use common sense and a reasonable level of discretion.
I may or may not have done this myself, and, or I may or may not know people who have.
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