I've done deliveries from Tortola to St. Petersburg, FL a couple of times. Also picked up a boat on Great Inagua and took it to Florida once. Of course, you are going through Old Bahama Channel, which is the best way to go. Wind should be off the quarter or stern all the way unless you get a norther, which can happen at the time of year you are going.
The last time through there was in a 32' Beneteau. We did the entire trip from Tortola to St. Pete in nine days. You should be able to hit Key West in five day from PR
. Forget the ice unless you stop at Great Inagua. There isn't much there though and if it were me I would skip it also and just plan on warm water and soda and food that doesn't have to be refrigerated after the ice runs out in a couple of days.