Add pineapple, banana, yogurt and ice to blender. Add 1 cup of the milk. Pulse until mixture is smooth. Add more milk about 1/4 cup at a time until desired consistency is reached (I wanted to be able to slurp mine with a straw and it ended up being about 1 1/2 cups of milk). Pour into a glass and drink up!
***DAIRY FREE OPTION: use coconut milk and leave out the yogurt.