Blend: Combine the frozen pineapple chunks, vanilla ice cream, pineapple juice, and ice in a blender.
Blend Until Smooth: Blend on high until smooth and creamy. Pause to scrape down the sides if needed to ensure everything is well mixed.
Adjust Consistency: Add more ice for a thicker texture, or more pineapple juice for a softer, creamier consistency.
Chill for Firmness: For an even firmer texture, transfer the mixture to a container and freeze for 20-30 minutes before serving.
Pipe It Like Disney: To get that classic Dole Whip swirl, scoop the mixture into a piping bag with a large star tip (or a Ziploc bag with a corner cut off). Pipe it into cups, swirling the mixture in a circular motion just like the original.
Serve: For an extra authentic experience, serve as a float by adding a splash of pineapple juice to the bottom of the cup before piping in the Dole Whip.