Using a blender, immersion blender, or food processor, blend together bananas and coconut milk until smooth.
Stir in strawberries and pineapple, then divide mixture among popsicle molds. Freeze for at least 4 hours, until set.
When ready to coat popsicles, remove popsicle mold from the freezer and set in sink to thaw slightly.
Make the chocolate coating by melting chocolate slowly in the microwave, in 30-second increments, stirring after each time. When the chocolate is almost completely melted, add the coconut oil, stir well, and heat again for 15 seconds. Stir until completely smooth. If you like, transfer chocolate to a tall jar wide enough to dip popsicles into. Pour sprinkles, if using, into another jar.
Set a sheet of waxed paper on a cookie sheet. Remove popsicles from molds gently and carefully dip popsicle into chocolate, then immediately into sprinkles (or press a cherry into the top).
Set finished popsicles onto waxed paper and freeze cookie sheet for 30 minutes, then remove popsicles to a freezer-safe container, with waxed paper between each popsicle.
Let thaw slightly before eating.
Dark chocolate chips contain no milk, but check the label for vegan certification if you are concerned with cross-contamination. The melted chocolate will harden immediately when it comes in contact with the popsicle, so work quickly. Any leftover chocolate can be stored, covered, in the pantry, and reheated if it solidifies.