Canning pineapple is one of the easier things to can. My family loves the flavor too. The only problem is that pineapple doesn't tolerate the cold in my area so I have to watch for good deals at the grocery store and stock up then.
How to Can and Preserve Fresh pineapple
The following directions will make a 1-pint jar of canned pineapple. This makes it easy to multiply the recipe for the number of jars you want to add to your food storage.

The first step is to use a sharp knife to cut off the ends and sides of the pineapple.

I then cut it into quarters.

Next, I remove the hard core from the quarters.

Finally, I slice the pineapple into small pieces.

Next, I place my peaches into my hot jar and top the pineapple with 3 tablespoons of sugar. Usually, one pineapple will fill 4 pint jars.

I fill the rest of the jar with hot water leaving a 1/2 inch of headspace. I wash the rims with a clean damp cloth so that nothing will interfere with the seal.
Finally, I place the lid on top of the jar and add the ring. Tighten the ring to fingertip tight and process in a boiling water bath for 15 minutes if at sea level. (Remember to adjust your processing time if higher than 1000 feet elevation.)

Once your peaches have completed the appropriate time in the boiling water bath canner, turn off the heat, remove the lid and allow them to cool for 5 minutes. Then take them out and set them on a heat resistant surface spacing them about an inch apart, for 24 hours to cool and completely seal.

If your jar of pineapples did not seal then place it in the fridge and use it immediately. Store the sealed jars in your cool, dry, dark pantry to enjoy for the next 1-3 years. After three years the nutritional value of canned food diminishes.
If you have any questions about canning with the boiling water canner or how to adjust the pressure or processing time for altitude, take a look at my canning basics videos.