First, I want to talk about how to pick a pineapple. I've read some weird things out there like smelling the leaves to see if they smell like pineapple. The best way that I've found to check for ripeness is the color. You want to see some yellow towards the bottom and maybe a little yellow in the centers of each little section. If the whole entire thing is yellow, it's probably over-ripe. If the whole thing is green, it is under-ripe. So you'll want to consider if you're using the pineapple today or later. If the answer is 'today,' then get the one that is partly yellow. If the answer is 'in a few days,' get the one that's green and wait for it to start turning yellow around the bottom.
Ok, now how do you cut this beast?! First, cut off the top and bottom.
Now, stand the pineapple upright and cut off the rough skin in strips. Once it is all off, go around once more and cut off and brown pits you may have missed. Then, turn it upside down and cut off any more skin you may have missed.
Lay the pineapple on its side and cut it in half width-wise. This step just makes the pieces smaller and therefore easier to work with.
Place the two halves on their flat side. Cut them in half length-wise, then cut them in half again so that you have quarters.
Now place a quarter on one of it's inner sides. With your knife at an angle, cut out the core. Repeat with the remaining pineapple pieces.
From here, you can cut each quarter in half length-wise, then cut into chunks. Or you can cut the quarters into thin slices. You could even leave the quarters intact and place them on the grill. Yum!
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