The whole pineapples in the grocery store may look a little daunting, but they're actually quite easy to cut up, and the taste of fresh pineapple is far superior to what you will find in a canned product. The method described below will yield pineapple cut into chunks (as opposed to rings).
The first real step is choosing a good pineapple. Color is not necessarily a good indicator. There are certain varieties that are still green when ripe. The real test is smell. I don't care if the grocery store is crowded, pick up that fruit and give it a good sniff. If it is ripe, it will smell of wonderfully fragrant pineapple. Pineapples won't get any riper once they've been harvested, so choose one from the store that's already ripe. It won't get any better on the counter at home.
Let's break down the pineapple. Begin by collecting your pineapple, a nice solid cutting board, a large sharp knife, a bowl for catching the newly cut fruit, and a bowl for catching the scraps. I also find it helpful to have a clean kitchen towel (or a few paper towels) handy for this task – it can get pretty juicy.
Lay your pineapple horizontally on the cutting board. Holding it firmly with one hand, begin by slicing off the leafy crown and enough of the flesh at the top so that only the yellow interior of the pineapple is showing after you've made your cut (no brown skin). Slice off the bottom of the pineapple in a similar fashion. This will help the pineapple stay nice and steady during the next phase of the procedure. Key to enjoying your pineapple breaking-down experience is keeping the mess in check as you're cutting. Throw the scraps in the scrap bowl as you go, and catch any sticky pineapple juice spills with your towel.
Next, with the pineapple standing vertically on its nice flat bottom, carefully slice the bumpy brown skin off the sides, following the curvature of the pineapple. Discard the skin and rotate the pineapple as you go. Take care to get as much of the brown tissue as you can without cutting away all your pineapple – this can be easier said than done! To help a bit, look at pineapple from the top down. You will see the spots where the flesh bumps out, and there is a tiny spike in the center of each of the bumps. This is called the eye. Put knife to pineapple in such a way that the eye is in the center of your slice and you're catching a bit of the ridge on either side of that one as well as you slice down. Skip over the ridge you partially sliced into and place the eye of the next bump in the center of your slice, catching the rest of the partial ridge as you cut. This may seem unclear at first, but crack into a pineapple and you'll see what I mean.
The pineapple is very slippery at this point, so exercise caution. With the pineapple still standing upright, cut it in half length-wise. Turn 90 degrees and cut in half lengthwise again, yielding four pineapple quarters. For each quarter, carefully cut away the fibrous core. The core is the inside corner of your pineapple quarter, and it is slightly lighter colored than the remainder of the pineapple flesh. After I've cut my core piece from the pineapple quarter, I test that I've removed all the fibrous material by gently poking along the cut with my knife. If it gives easily, the core is removed. Repeat this with the remaining quarters.
Finally, for each quarter, lay it out flat on your cutting board, and cut it into lengthwise strips, roughly 3-4. With the strips laid side by side, carefully slice across the strips to produce your lovely pineapple chunks. It is important as you begin to slice the chunks that you taste test your pineapple repeatedly to make sure it is sufficiently juicy and sweet.
Don't be too terribly surprised if your scrap bowl has more stuff in it than your pineapple bowl. For my 5 lb pineapple, I wound up with about 2 lbs of fruit.
If you want the fancy pineapple rings instead of chunks, probably the easiest method (short of buying a pineapple corer) would be to follow the steps above through cutting the skin from the pineapple. Then lay it horizontally and carefully slice it. From there, with a small paring knife, trace around the core to remove it (it will be easily recognized in the slices). To be honest, I've never tried making pineapple rings, but another thing that *might* work would be to take a 1 ½" to 2” round cutter and use it to cut around the core in each slice (though this might result in crushing out some of the pineapple juice, which would not be ideal).
When done cutting up my pineapple, I store it in an airtight container in the refrigerator till I'm ready to use it. Sometimes, if I don't think I'll use it quickly enough, I will freeze some of the pineapple and use it as a tropical additive to my smoothies (though the flavor is much more distinct if you eat it fresh).
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