Lizz/kev...you can't go to PR or the BVI's via sea unless you go out to about 60 west to get the proper trade wind angle. There is no other way to PR except on the thorny Path...so it is pretty hard to end up at the T&C by accident...you need to choose one path or the other and if you are going the sea route you are much better heading out from Beaufort to 60W than trying to bash your way out from the Bahamas.
Assumig that you are not prepped for the sea route...then you will be going down the Thorny Path and you can make either Puerto Plata OR Luperon from the T&C with the right weather but there is NO way to make Puerto Rico without a stop in the DR and several hundred miles of easting into the trade winds and seas (as VanSant makes clear.) May I also suggest that once you make it to the EAST end of the DR and prepare to cross the Mona Passage, that you do not go ashore or leave your boat unattended in Samana. Simply
anchor and rest and make your passage at the first opportunity.
We managed to make it from Luperon to the south shore of PR (Ponce...which was WONDERFUL) thanks to weather routing from Chris Parker (contrary to all of VanSants advice!) so I would suggest him as a resource for you on
SSB or via e-mail as you make your way:
ssb.html" target="_blank">http://www.caribwx.com/
ssb.html
Good luck on the voyage and keep us posted on your progress!