If using a fresh pineapple, remove the fruit and cut into small pieces. Spread them over a tray or a silicone cake pan (ideally, with some space between them) and place in the freezer until frozen solid.
If you'd like to serve the ice cream in the pineapple, slice the pineapple in half lengthwise and carefully remove the fruit without cutting the rind. A spoon helps.
Make the sorbet
Add the frozen pineapple chunks to a food processor. Start processing the frozen fruits with your food processor.
Slowly add in a dash of coconut milk and blend until you get a creamy consistency. (Add slowly as adding too much will result in a slush rather than a scoopable ice cream.)
Serve immediately or store it in the freezer for later.
If you choose to store the pineapple ice cream in the freezer, take it out several minutes before serving to allow it to reach a creamy consistency again.
Video
Notes
Serving options
If you want to serve it in the pineapple, fill the hollowed-out pineapple with your ice cream. Freeze the filled pineapple long enough to make for easy slicing. Slice in half lengthwise to give pineapple quarters.If you're feeling fancy, you can also use a piping bag to pipe the ice cream into small bowls for serving. This gives it more of a soft-serve look, and a "Dole Whip" feel. The mixture can also be made into popsicles by pouring it into popsicle molds and storing in the freezer.