I don't think that there is a better place on the Internet to be asking this question. Considering that the name of the site "Mahalo" itslef derives from the same people who are famous for pineapples, you certainly deserve a good answer.

On the inside, a ripe pineapple looks like this:
http://www.botany.hawaii.edu/faculty/webb/BOT201/Angiosperm/Fruits/PineappleFruLSMacro240.jpg

Many grocery stores will prepare pineapples by coring them, placing them in plastic containers and keeping them cool or on ice. If you come across these, they are often the easiest pick.

To choose an un-prepared pineapple:

Smell it. It shouldn't smell fermented like old wine or vinnegar.

Touch it. It should be firm, not soft.

Look at it. It should have a consistent colour without any irregular dark spots or noticeable inconsistencies.

Some folks will tell you to pull a "leaf" out from the top. If it pulls easily, it's ripe. While this is true in some cases, depending on how pineapples are stored the leaves can release without the fruit being ripe.

Last, and this is of course going a bit overboard.... ask the produce manager when the pineapples came in. Pineapples cannot ripen "on the truck" like other fruit and when they are picked, they are ripe. That's it. Every day that they are in transport is one day of over ripening.

I hope that this helps.
Source(s):
I worked in a couple of produce departments while going through school.

I also just got back from Hawaii where I visited the Dole Plantation. They schooled me on Pineapples!

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