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Step 1
To freeze a fresh pineapple, remove the skin and the core, then cut it into uniform chunks. Place them on a parchment paper-lined baking sheet in a single layer. Make sure the pieces are not touching each other. Allow the pineapple to freeze for 6 hours or overnight. Once they are frozen, you can toss them into a freezer bag until you are ready to use them.
Step 2
When you are ready to make the Dole Whip, add the ice cream, pineapple juice, and frozen pineapple to a blender. Blend until well combined and smooth.*If it is too thick, you can add a little more pineapple juice until you reach your desired consistency.
Step 3
Scoop into bowls or glasses, add chopped pineapple and cool whip (if desired), and serve immediately.
Step 4
For a more authentic Dole Whip experience, use a piping bag and a large star tip, swirl into the bowls or glasses, and top with pineapple (optional).**If you are pipping the Dole Whip, freeze for 30 minutes before pipping it into the bowls so it holds its shape better.