Join Date: May 2002
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Maintaining head to wind
I usually like to raise the mainsail before leaving the dock or mooring. Situate the boat so that, if you let all docklines go except the bow line, the boat vanes with the bow into the wind. Raise the mainsail, let go the bow line, push the boom away from you and sail away under main alone.
To raise the jib, I like to put the boat on a course between a beam reach and a close reach. Then I use a tiller tamer (or a bungee cord will do) to hold her on course while I raise the jib.
It sounds like part of your problem is that you have to go forward to the mast to raise and lower the sails. If the halyards are led aft to the cockpit, then you will be better able to raise and lower sails without going forward.