I like mine perfectly ripe. I know its ready when I pick it up and smell it. It will smell sweet and ripe. Sometimes it will smell sweet but it doesn't have the ripe smell and I don't cut it just yet. Don't cut into it too soon, it might be sweet but have some sourness too. When the smell is ready, the pineApple usually has a dark green color, and the leaves are starting to brown.
Be careful how you store the pineApple waiting for it to ripen. If stored wrong, the bottom can start molding. If that happens you can cut it off but you will have less pineApple to serve. Store it on a rack, like a cooling rack used for hot baked goods. That way air can flow freely around the pineApple.
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