To a blender, add bananas, pineapple, yogurt, milk, and vanilla, and process until smooth. Add additional splashes of milk or pineapple juice, as desired, to thin.
Add cherries and stir until just combined (careful not to overmix as this will turn your popsicles pink!)
Pour mixture into popsicle molds and freeze for 4-6 hours, or until set.
Once frozen, melt chocolate in a microwave-safe dish, in 15 second intervals, until fully melted.
Allow chocolate to cool slightly before dipping popsicles. Sprinkle immediately with toppings. Enjoy!*If your melted chocolate is somewhat thick when melted, stir in 1/2 tsp coconut oil to thin. Mixture should be semi-thin for easy dipping.