Puree the pineapple, half the maple syrup and half the vanilla in a blender until smooth.
Puree the frozen cherries with the remaining maple syrup and vanilla.
Add the pineapple and cherry mixtures to the popsicle molds in layers.
Freeze the popsicles for 2 hours.
Run the popsicle molds under warm water when ready to enjoy to make it easier to remove them!