I am going to Cuba LEGALLY for a holidays/new years trip. It is not the 70s anymore and it is fairly easy to obtain permission from the Treasury to go. I am going through YYZ. If you haven't booked a trip yet
http://www.grupotaca.com had cheap flights from YYZ to HAV ($401 coach $620 biz)on LACSA.
As long as you don't get your passport stamped by the Cuban immigration, you should have no problems. Go for it!!!!!!!
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"I just wanna wish you good luck, we're all counting on you"
-Dr. Rumack