Depending on your stamina, provisions and desire to stop at Bermuda, if you get a big, slowly rotating low to the north out of NJ behind you, you might find the sailing good enough to head
straight to PR past Bermuda. You could find yourself not changing the sail set so much as just curving the heading more and more to the south.
You could do worse than to leave (weather permitting) ahead of the Carib 1500 and to "piggyback" on their race
as SpecialD suggests. An SSB
listening to Herb's weather
and to the report of Carib 1500 boats in a 100 NM circle around you (even if you never see them) is a great "herd" technique by which you can refine your own routing. We used this to find 25 knots of wind
instead of 35-40 knots, because our objective was "fast, safe passage", as opposed to "grab a pennant". So being a cruiser in a widely dispersed fleet of racers in blowy weather, along with possessing the means to monitor
their progress and met reports, I found invaluable. So did our skipper
, who broke a number of his boat's 24 hour distance records thanks to finding the Goldilocks zone in terms of wind
and sea state when all about was fairly agitated.
Bring spares, and plenty of 'em.