Join Date: Nov 2007
Location: SF Bay area
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You can totally get somebody to hoist you. Sending the lightest crewmember is nice if you happen to be the lightest crewmember...
If you have the option, choose an all-rope halyard. If you don't have that option, carefully inspect the rope-to-halyard splice before going aloft. Also, like Faster suggested, it's very helpful to pull on the descending part of the line. I can almost hoist myself up doing this (but it's nice to have somebody tailing the line on a winch). This only works if it's an all-rope halyard, unless you're comfortable hauling a wire rope in your hands.
Assuming you have two crew members on winches, I find that the easiest thing is for them to alternate tensioning the halyard and then taking up the slack created by the other's tension. A small ratcheting motion is good for this and you can get into a nice rhythm to the point where the hoist is almost continuous. Use the smallest winches that will take the load: for a given size winch handle, a smaller-diameter winch provides a larger mechanical advantage.
Here's an idea I've heard but never tried: take a rope with loops in both ends with you. When you get to the top, put the rope over the masthead and put your feet in the loops. I guess the rope should be about one and a half times your height. Now you can stand in the loops instead of sitting in the chair.
Plan which side of the mast you want to be on and plan how you'll have to switch halyards when you get to the spreaders. Ditto for the trip down.
The descent, as Wayne mentions, is controlled by the deck crew.
I should reiterate that you should take your multimeter with you. And a spare bulb. And some duct tape. And a set of screwdrivers. And a camera, so you can take pictures of the other things you realize you'll need to fix.
s/v Laelia - 1978 Pearson 365 ketch