How to Make a Pineapple Cup, as well as four different drinks to serve in it.Run a knife around the inside of the pineapple, about 1/2 inch away from the skin, in a circular motion.Cut all the way down to the hard portion at the bottom of the pineapple – DO NOT cut all the way through the bottom, or you’ll end up with a pineapple sleeve instead.After you’ve sliced all the way around, you may go on to cutting the internal core.