I've done that trip several times. Catching a front at the time of year you plan to go should be easy. The downside is the way the gulf stream gets roiled with a north wind. However, once you get through the Providence channels, it's a pretty good sail.
Now here is the secret. I found in every trip that time of year that the wind goes to the east/northeast at night once you get into the more southern latitudes. That will allow you to head more directly toward your VI destination. The downside is you still will be beating most the time unless you are lucky to make it far enough east on the front, so you can head directly south.