With all due respect FSMike I have been sailing for over thirty years in the Great Lakes and have grown up around boats my hole life. I find your comment very insulting, .
Yes, sometimes this forum beggars belief.
Going by the Azores and canaries is the easy but long way.
I havent done Nova Scottia to bahamas/Caribbean direct but the time to go is at the end of the hurricane season and before winter. As you'll note both seam to overlap!
Its only 1,500 miles so not far.
The route is down to 65 West (about where bermuda is, so a stop in is on the way, if desired to wait for a weather window), then direct to Georgetown in the southern bahamas.
Prevailing winds: up the bum to start, then variables and a tad on the nose and then up the bum from Bermuda.
Contrary to what some posters have written the gulf stream is well coastwards of the route except for the first three hundred miles, where it is on your beam and would help not hinder by keeping your easting.
The difficulty is if you hit a north atlantic storm from the great lakes, or a late hurricane, or as with Sandy, a combination of both.
The Azores, canaries, bahamas route is 5,400 so a completly different type of voyage. If you do that then stop in the Med for a season.