An elegant rotation around the mast ending with a tail first landing, the Cheese-Roll unfortunately has been considered inferior to a forward loop. Hogwash, this is a great maneuver victim to a bad name.

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Rider: Royn Bartholdi

Steps

1) Unhook, and look for a ramp. Make sure you have room to perform this move. As you approach the wave you are leaning a little forward toward the front of your board. Make sure you're amped because you have to throw this move hard -- commit like a warrior in battle.

2) Jump off the wave and lean the mast away from you while sheeting the clew toward the tail of the board. This is like a Laydown-Jibe in mid-air.

3) Now jump over the mast between the gap between your mast and board nose, pulling the clew-hand with you. In other words, keep sheeting in the sail with the back hand and pushing out with the forward hand. Look under your arm pit.

4) The sail will rotate and get backwinded. Remember to commit, and to keep sheeting the sail in with the back hand.

5) The rig will flip around the axis of the mast until you are back to where you started.

6) Open up the sail by sheeting out with the back hand and bringing the mast forward as you land.

7) Bend your knees as you land.

8) Bend your knees as you land.

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Tips

I learned this maneuver after the Forward Loop but a lot of sailors learn it first.
Look anyplace in the direction of your rotation: Under arm pit, over your shoulder, etc... Just do not look at the water.
This move has less risk than a Forward-Loop because it is performed closer to the water.

Ideas

Try this move at different angles to the wind.
Try the stalled Cheese-Roll.
Try the double Cheese-Roll
Let go of the front or rear hand.