[quote=Dogboy]The closer you can get the boat to directly head-to-wind, the easier raising the mainsail will be. Within about 15-20 degrees of straight into the wind is ideal. Much more than that and the sail will start to get pressure in it which will cause more drag against the mast track and possibly against the shrouds, etc. Depending on what type of boat you have, getting the bows pointed directly into the wind may also be necessary for engaging the halyard once the sail is fully hoisted (i.e., if you have a hook & ring system like on a Hobie 18, the boat really needs to be pointed into the wind to get the hook to engage/disengage).
I would not try to hoist the sails with the boat bobbing out in the water, it's a recipe for disaster as the boat will almost certainly drift off of a head-to-wind heading.
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