In a blender, combine the frozen pineapple chunks, coconut milk, sugar, lime juice, and vanilla extract (if using). Blend on high until smooth and creamy, scraping down the sides as necessary. This step is crucial to ensure a uniform texture.

If you prefer a firmer texture, transfer the blended mixture to an airtight container and freeze for about 30 minutes. This allows it to thicken slightly.

Scoop the Dole Whip into serving cups. You can use a spatula to help transfer it smoothly. For an authentic presentation, consider piping it into the cups.

Optionally, garnish with a slice of fresh pineapple or a cherry on top before serving.