Originally Posted by TerralTheSeeker
Practicing my heave-to over and over again, I tried letting the boat slow way down after letting out the main, then turn the tiller to leeward. From appearances, it seems that even with the main let out there's still enough forward speed to cause the boat to turn into wind when I go leeward with the tiller. I waited and waited and could still see the boat moving at what seems a good pace with the main let "all the way out" (the sail pressing up against (and stopped by) the shrouds).
You need to STOP the boat to heave to (or nearly so). make a slow tack leaving the jib alone so that it becomes back winded. When you are head to wind, keep the boat pointed here until you are almost stopped, and then just barely let the back winded jib fill and then work the tiller to leeward.