Cut half-inch pineapple slices using a large knife. Hollow the core, trim the edges, and then cut into small triangles. Stick a lollipop stick into each pineapple wedge, pat dry, and set aside.

Dip pineapple pop into melted chocolate until halfway covered and lay on a baking sheet lined with Gefen Parchment Paper. Sprinkle with coconut flakes. Refrigerate to set.