the eastern tradewinds are your friend if you are headed to Brazil...fastest way but roughest is maybe just skirt Cuba and then maybe head for jamaica..then on down...next stop maybe Trinidad...
Geez, what do you have against this guy, that you would put him through such misery? (grin)
I would certainly not recommend a transit of the Old Bahama Channel, especially to a newb... Very little margin for error there, tons of shipping, that's a pretty nerve-wracking passage, although as a Canadian, he does have the advantage of being able to stop in Cuba if need be... Still, I consider that to be a very hazardous route, against the trades...
Then, why head to Jamaica? Not only would you be giving up easting, but you'd further degrade the very tight sailing angle to the east... Looking at a chart of the entire Caribbean basin, I'm hard pressed to select a more arduous passage than the beat into the trades from Jamaica to Trinidad...
Only 2 real choices, IMHO... Either the Thorny path to the Lesser Antilles, or the offshore route described by Don Street and others, out the NE Providence Channel in advance of a cold front, riding it as far east as possible, then tacking south and hoping you fetch up in the Virgins, or thereabouts...
I'm not sure those who are encouraging him to "Just Do It" have any real appreciation for how difficult a voyage this might be, especially for someone with minimal sailing experience... It's one thing for a newbie to start out with a downwind voyage like the one from SoCal to Baja, but it's another thing entirely to suggest that their first ever offshore sailing be the bash back north, instead... Hell, every year many cruisers with considerable experience attempt to sail from S Florida to the Eastern Caribbean, and never make it beyond Georgetown, or Luperon... In a season where the trades are really kicking, that can be a pretty brutal trip...
If this guy is really determined to do this, I think a far more sensible approach would be to find a boat in a place like Annapolis, then get his feet wet sailing down the east coast... If he's a quick study, then perhaps by the time he's reached Florida, he could attempt the route offshore from the Abacos/NE Providence...
Or, should he choose the Throny Path route, perhaps by the time he gets into the SE Bahamas, he starts to wonder if it's worth it to beat a couple of more thousand miles into headwinds and adverse current just to attend a couple of soccer matches, and comes to the realization that it probably doesn't get all that much better than right where he is, right then... (grin)