Place all ingredients in a high powered smoothie blender and puree. Add a small amount of additional milk to help thin out the smoothie, as desired.
Note: I like to puree without the kale and then add in small additions to ensure that it doesn't change the color when serving to kids. You can alternatively use a green smoothie powder to add the greens without the color.
Recipe by Good Food and Family Fun at https://goodfoodandfamilyfun.com/pineapple-cherry-smoothie/