Could I sail from Ontario to the Carribean?

It is “sailing” because it uses solely the wind. And there are boats which sail directly upwind. I have posted links before.

pure ignorance on my part, but could you avoid the gulf of st. lawrence by taking a right on the Richelieu river towards lake champlain and the Hudson river? Would it be quicker? Would it be sailable?

I would have guessed no, but, yes, you can using the Champlain Canal. (I am presuming that my memory that the Richelieu is navigable through Quebec to Rouses Point is correct.)