My friends from Virginia..flew through YYZ...
...however one issue to consider is when you are returning home from your winter trip to "Canada" how do you explain that amazing tan? They got a way with saying they were skiing all week in the sun...but be prepared to get the question. The real value of Cuba is to go to an all inclusive which are very cheap from Toronto. My friends just used their points IAD-YYZ and then booked an all inclusive using a Toronto travel agency. I have to say its one of the few things thats cheaper in Canada than in the US is all inclusive vacations, simply because we have charter airlines that service this business exclusively. Also you do not get a stamp in your passport, the only penalty is the 10% surcharge when changing $US. Have fun...Cuba is a nice place filled with very friendly people.