It's not a hell of a dilemma but its would be un upwind passage
unless you are going to the western half of the DR.
In November there's plenty of NE winds so it shouldn't be too bad at all. Have a look at the pilot chart.
If you go across Silver Banks you won't see any whales as they will have all gone north by then. Those banks are one of the most heavily wreck infested in the world as the Spanish galleons needed to go quite close and if their nav was a bit out they would be a bit dead... So if you stop for a dive please remember to offer the government
a share of the gold you find!