Place the pineapple (with pineapple slices and juice from the can if you are using canned pineapple) in the blender.
Also add milk, honey (or sugar) and vanilla extract.
If you are using ice cream, add that also to the blender.
Blend until smooth and creamy, transfer to glass cups and serve immediately!
If you are serving the pineapple milkshake later, make sure to refrigerate the milkshake until ready to serve. For the best results, you may blend it again right before serving.
For longer storage, you can transfer the milkshake to ice cube trays, freeze and save for later use.