As above, the last thing you want to do is go south against the Gulfstream. Close to shore one can often find a counter current that will help rather than hinder your trip. Once you pass Key Largo the current comes more and more from the west instead of south on as off the Fla coast, so it will be a situation of wind (east generally) against the current and the seas could get up a bit. Again, close to the reef is calmer, but requires a lot more attention to keep from hitting a reef.