In a high-speed blender, combine the coconut milk, pineapple juice, pineapple chunks, pineapple gelatin, and pure vanilla extract. Blend until completely smooth.
Carefully pour the mixture into ice cube trays. Place the ice cube trays into the freezer. Freeze for 4 to 6 hours or until firm.
Remove the trays from the freezer. Transfer the frozen pineapple cubes back to the blender. Pulse until the consistency is grainy. Add non-dairy milk of your choice in 1/2 cup increments blending until the mixture has a smooth and creamy texture.
A homemade dole whip will be sensitive to heat and melt quickly. Serve immediately or keep it frozen. Enjoy!