To a blender, add pineapple, coconut milk, sugar, and rum. Puree until smooth.
Pour mixture into molds. Insert sticks. Freeze until solid, about 6 hours.
For the chocolate dip: Combine the chocolate chips and oil in a microwave-safe bowl. Microwave in 20 second intervals until melted and smooth. Cool slightly before dipping.
Line a large baking sheet with parchment paper and set aside.
To unmold the popsicles, run some hot water over the outsides of the molds, then pull to release the popsicles. Dip the top of each popsicle in melted chocolate and place on prepared sheet. Sprinkle with toasted coconut chips. Place tray in freezer until chocolate hardens.
The amount of popsicles will depend on the size of your molds.