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Step 1
Locate and attach the main halyard. The main halyard is the line that runs from the top of the mast down to the boom of the sail. Usually, it's clipped onto the end of the boom when the sail is down. Unclip the halyard from the boom and clip it to the triangular top of the mainsail, called the "head."
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Step 2
Release all down-pulling tension. In most cases, you need to locate and release the mainsheet and boomvang tension before hoisting the mainsail. The boomvang is located at the front of the boom and connects to the mast. Uncleat it and let it out. Do the same with the mainsheet at the end of the boom.
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Step 3
Put the boat into the wind. The sail must be completely depowered before raising the main, especially if you're already out on the water sailing (under jib or motor power, for instance). Locate the direction of the wind and put the bow of the boat squarely in that direction.
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Step 4
Hoist the mainsail using the halyard. Find the halyard line that runs towards the cockpit of the boat. You can give a couple different lines a tug to see which moves the head of the sail that's connected to the halyard. Raise the main up by pulling hand over hand. When the resistance begins to stiffen, wrap the halyard line around a winch and use the winch to gain some mechanical advantage.
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Step 5
Check the head of the sail and brake the halyard line. Look up to see if the mainsail reaches the very top of the mast. If the mainsail is fully raised, then cleat off or brake the mainsail halyard, coil it or place it out of the way so you can sail.
