I've thrashed my way up-wind on the south-side of St. John in a Moorings 40CC monohull.
We got slowed to a crawl at the SE tip of STJ, I forget the name of the point of land there.
Anyhoo... it's tempting to stay close to land, but the water pours around that point. It's better to stand out to the south a few miles on a really long tack. All of this is pretty much open ocean. It's spirited sailing if you like bashing into 6-foot seas.
I managed to get half our crew sick in 2000 doing this... <img src="http://www.traveltalkonline.com/forums/images/graemlins/duh.gif" alt="" /> <img src="http://www.traveltalkonline.com/forums/images/graemlins/jester.gif" alt="" />