Gather all ingredients and equipment.
Place the frozen pineapple chunks in a blender.
Add the coconut milk to the blender.
Pour in the sugar (or honey) and lime juice.
Add the vanilla extract for flavor.
Blend the mixture on high speed until smooth.
Stop the blender and scrape down the sides if necessary.
Blend again until the mixture is creamy and thick.
Transfer the Dole Whip into a serving bowl or cup.
Top with whipped cream and a cherry for garnish.