I could not find very much on the web about the best way to cut a pineapple into chunks so I decided to use this forum in order to pass on the secrets of the island boys who do this for a living. This skill has been passed from father to son for generations but is in danger of being lost in our modern mechanized world.
Island Boy Tip: Please be careful when using a knife for any purpose. You must respect the blade. It can cut you.
Step 1: Be Sure to Choose a Ripe Pineapple
Island Boy Tip: You can tell a ripe pineapple by the smell. Just sniff the bottom (stem) end and if it smells like fresh sweet pineapple, it's ripe. If not don't buy it. Pineapples ripen on the plant before they are picked and will not ripen further. Make sure the flesh is firm, not soft. Don't worry about the brown leaf tips.
Step 2: You'll Need Two Tools
1. A large knife to cut the pineapple into sections.
Island Boy Tip: Use a serrated bread knife unless you have a razor-sharp machete or chef's knife.
2. A small knife to cut the sections into chunks.
Island Boy Tip: Use a fillet knife or thin boning knife.
Step 3: Lop Off the Leaves
Island Boy Tip: Leave a small section of leaf stem on the end. This will hold things together.
Step 4: Cut the Pineapple in Half
Step 5: Cut the Halves in Half
Step 6: Cut the Quarters in Half
So now you have eight sections.
Step 7: Insert the Filet Knife Into the Leaf Stem End of One Section
Island Boy Tip: Insert the knife below the central core and above the outer skin. This is the secret to keeping everything together at this point. This makes the following steps much easier. You won't find this tip anywhere else.
Step 8: Cut Forward Away From You
Island Boy Tip: Go close enough to the skin to keep most of the flesh but don't go too close or you'll get undesireable eyes in your chunks.
Step 9: Cut to the Other End of the Core
Island Boy Tip: Continue cutting away from you, then go up toward the core but don't cut through it.
Step 10: Cut Back Toward You Below the Core
Slowly! Be careful not to cut yourself! When you get half way through, grasp the section at the other end and continue cutting toward you.
Step 11: Cut All the Way Back and Cut Through the Leaf Stem
Hold the section in the middle while doing this.
Step 12: Cut Through the Core at the Other End
Step 13: Remove the Core Piece
Step 14: Cut the Flesh Into Chunks
Island Boy Tip: Cut down and pull the knife toward you slightly. Cut just above the skin but not all the way through it and chunks will stay put.