Hi Courtney,

I've done exactly that route once about 10 years ago while helping to deliver a friends 44' Cat. It will not be a pleasant trip, as the wind tends to be on your nose the whole way. If you are really committed to this route, I suggest you read Bruce Van Sant's book "The Gentleman's Guide to Passages South" to help with a strategy to ease the pain a bit. 

I'd suggest you take an easy trip up to the Chesapeake in the fall, and possibly join the Salty Dawg rally from Hampton to the BVI around Nov 1st. This is a much easier trip, and if you want to head to PR, just adjust your course a few degrees at the end. We did exactly that, and completed the trip in 9 days. The Salty Dawgs offer free weather routing from Chris Parker, some great seminars, and even better parties. You also can't beat the price, as it is free, or something like $250 if you join the Salty Dawgs, and for that, they offer enough negotiated discounts to more than reimburse you. Most years they have 80+ boats heading down. 

Best of luck on your trip south. 

Steve Davis

Aloha SM72

Aruba