Peel the pineapple length wise to remove the skin. Remove the eyes deep and cut the fruit to 2 parts. Then to quarters. Remove the core and set aside to use it for juicing. Chop the pineapple to cubes. Do not use the core in your milkshake.
To make the vegan milkshake, soak cashews in warm water for 15 to 20 minutes. If using almonds soak them for 3 to 4 hours in water and peel the skin. Add them to a blender along with ¼ water and blend as smooth as possible.
Add pineapple chunks to the blender along with sugar, vanilla or pineapple extract and 1 cup more water. Blend until creamy and frothy. Add more water if desired.
Add the pineapple chunks, chilled milk and ice cream to a blender jar.
Blend until smooth and creamy. If need add more milk to adjust the consistency.
Pour to serving glass and enjoy.