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.
My
advice 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.