Line an 8 x 8-inch baking pan with parchment paper. Mix the coconut oil, chocolate, and 1 tablespoon of maple syrup together in a small bowl and set aside.
Puree the bananas until smooth in a blender with 5 tablespoons of milk then spoon into parchment lined pan and spread evenly.
Rinse the blender, then add the strawberries, 3 tablespoons of milk and additional tablespoons of maple syrup, pureeing until smooth.
With a spoon, swirl the strawberry mixture into the banana base. Drizzle in the chocolate mixture in an opposite swirl pattern then use a spoon to incorporate into the banana and strawberry with a swirl motion.
Top entire mixture with crushed pineapple. Sprinkle crushed peanuts on top and place cherries evenly with the cut side down. Cover and freeze for at least two hours. If freezing longer, thaw in the refrigerator for 15-30 minutes to soften slightly before serving.