First, you have to peel the pineapple.
Cut off the top and bottom of the pineapple and set it upright on your cutting board Using a sharp knife shave the skin off from top to bottom, following the contour of the fruit
You then have two ways to cut it into either rings or chunks: Pineapple Rings
Next, you lay it sideways and cut it into slices as thick as you wish.
You then use a paring knife to cut out the corky centers of each slice.
You now have a pineapple ring.
Pineapple Chunks Next, cut it lengthwise down the center.
Cut out the exposed corky center.
This can be done with a V-shaped cut.
You can then break down the fruit into chunks as desired.
Here is a step-by-step guide with photos: http://howtocutapineapple.com/
Here is a step-by-step guide on video: http://www.youtube.com/watch?v=AJJ-iQkbRNE
cooking.stackexchange.com/users/60/hobodave
I never cut rings -- I always cut pineapple
so it's more like a pickle spear.
(I find it easier to grill that way) trim the bottom of the pineapple, so it sits flat on the cutting board.
(don't trim the top, it's a useful handle)
Hold the top, and take a sharp knife, and start at the top, slicing down along the outside edge ...
you start going out, then down, then back in, to follow the shape of the pineapple.
Depending on what you're going to be doing with it affects how deep you need to cut.
(I've never had a problem with the occassional little brown circle; if you want to cut those off, feel free, though).
cut off the top of the pineapple
set it back upright again, and cut it down the middle, then rotate 90 degrees and again, so you have 4 quarters.
slice out the center of each of the quarters ...
you should see a slightly lighter bit ...
that's the core, and it's kinda tough, so you want to take it out.
slice the quarters into sticks
, then chunks if you want.
munch on the cores you removed when no one's looking.
(it's not all core, so I kinda nibble on the edges)
cooking.stackexchange.com/users/67/Joe
All the other answers say "Step 1 - peel the pineapple.
" I don't do that.
Instead, I make what our family calls "boats".
In addition to being a pretty presentation, it's a way less messy way to handle the fruit; you're not wrestling with a peeled and juicy pineapple and you lose way less juice.
We cut pineapple this way even when we intend to toss the chunks into fruit salad or something.
Cut the pineapple lengthwise in half.
Do not trim or cut anything else off yet.
The leaves, bottom, all the skin are still on and you actually cut the top leaves in half too.
Cut each half lengthwise in half.
Now you have four wedges, each a quarter of a pineapple, each with a tuft of leaves at the top.
Lay a wedge skin-down on the board.
Make a vertical cut partway through (just to the skin) close to the bottom, separating the bottom you might otherwise have trimmed off from the main body of the fruit, but don't cut through the outer skin
Make a similar vertical cut by the top, again not cutting through the outer skin
Holding your knife parallel to the cutting board, get under the corky triangle at the top of your wedge and cut it away.
Because the main part of the pineapple is still attached to the skin, this is easy to do Make a lengthwise cut (from the leaves to the bottom) straight down (from where the core was towards the skin) but as before stop when you reach the skin.
At this point your wedge has the core removed and has two spears that are only connected on one side to the outer skin.
If you want spears, slice underneath them to free them from the skin.
Assuming you want chunks, cut vertically repeatedly (again stopping just before the skin) to make the spears into smaller pieces, then slice underneath them to free them from the skin.
You can now turn the boat over and drop the chunks and juice into whatever you want the pineapple for, or simply put the boat on a plate and serve it to people.
Optionally, give them toothpicks to spear individual chunks with.
If you really want to show off, push every other slice to the left or the right so that the slices are staggered and easier to pick up.
There are some pictures at http://pinecreekstyle.blogspot.ca/2012/05/pineapple-boat.html though that person does the steps in a slightly different order than I do and takes the leaves off.
cooking.stackexchange.com/users/304/Kate Gregory
if you're not going to use a pineapple corer (which I don't), grab a sushi or a long sharp knife, and: deskin the pineapple like you would cutting a donair cut a square around the core push the core out
Now you have a hollow cylinder if you want chunks the type you put on a pizza: Cut the pineapple with the required thickness and then just chop it like you'd chop a tomato or mango
cooking.stackexchange.com/users/87/dassouki
A slightly different technique than the one in hobodave's post.
a picture speaks a thousand words: http://www.youtube.com/watch?v=GViaOUTC3rY
this technique gives you a nice looking pineapple at the end, with the pieces able to be eaten like a lolly.
cooking.stackexchange.com/users/210/Sam Holder
Pineapple Rings Pineapple Slicer
This thing is sweet.
cooking.stackexchange.com/users/None/
I wanted to cut up a whole, fresh pineapple, but wasn't sure exactly where to start without butchering it up badly - I wanted to cut it up into nice pieces!!  Are there any techniques that would work that would enable me to be able to cut it up into nice chunks?
How do you cut/process a whole pineapple?
cooking.stackexchange.com
<cutting><pineapple>
cooking.stackexchange.com/questions/6503
cooking.stackexchange.com/users/177/AttilaNYC
A pineapple slicer and corer will make this job easier, but otherwise you can cut off the top and bottom, then shave off the skin from top to bottom while following the contour of thefruit, then cut a square around the core, push it out and cut the pineapple into rings. Start by slicing off the skin and cutting down into the middle to remove the core.
You can buy utensils, such as a pineapple slicer, that will cut the pineapple into rings. Otherwise, start by slicing off the skin and cutting down into the middle to remove the core.