Is it possible for a US passport holder to travel to Cuba from Canada?

Is it possible. Sure. Just how legal it is......iffy at best.

I am technically a US passort holder, as an American, but I also hold an Italian Passport, since I have citizenship there, and currently live there.

Nothing prevents me from traveling to Cuba, as an Italian Citizen.

Sure,

the same way it's possible for a US passport holder to catch a little girl, rape her, then cut her up in pieces, store them in the refrigerator, and eat them one by one. It's just as illegal, and if the DHS computer detects a US passport number in the flight manifest -- which it will, as the two countries share their travel databases -- the red lights will go on and the men in black will want to have a chat with the US passport holder once he or she sets foot on US soil again.

Yes. Be aware that while travel there is legal, as soon as you spend any money you are breaking the law, violating the embargo, and subject to fines.

However, these days tourists are rarely penalized for violating the embargo — the Obama administration has focused its enforcement efforts on businesses. Just don't try to bring anything back!

Thousands go from Florida. No reason to go from Canada or Mexico unless you do not meet the

requirements. See this: http://insightcuba.com/

Yes it is possible, but not from the US.

It is very common to do exactly that.

yes, but why