Combine all the ingredients in a high-powered blender (in the order listed); blend until smooth and ultra creamy, pushing down the pineapple chunks if necessary, about 3 minutes.
At this point you can pour into dessert cups. But I like to freeze the mixture for 30-40 minutes, then transfer to a piping bag with a 1M “star” tip (to get that iconic Dole Whip swirl.)
Swirl into glasses.
(To help the soft-serve hold its shape even longer, freeze the swirled whip another 20 minutes.)
