If by "thorny path" you mean down through the Bahamas/T&C/DR/PR/USVI...then I would say that you will be hard pressed in the Vega once you make the turn at the DR.
I don't know your background...but steady trade
winds and seas make it impossible to make ANY progress for significant periods of time and when you do get a travelling window, you need to make the most of it before things close down again. So...you must be prepared to wait and not be under time pressure to be somewhere.
I am not aware of any Cuba route
that works and does not require even MORE windward beating.
From where you are, the offshore
to "route 60" and then south plan doesn't work
very well unless you can carry enough fuel
to get you east a good bit of the way.
would be for the Thorny Path...and a good read of "A gentleman's guide to passages south" given the size of your boat
and the need to make the most of favorable winds.