Prep time: 5 minutes
Total time: 25 minutes
6 ounces white rum
2 ounces coconut milk
2 ounces fresh lime juice
1. First things first: core your pineapple. The pineapple itself is going to be your glassware. This is hard to do, to be honest, so be careful and don't stress out about it, ok? You can always just use a Collins glass if you really want.
2. Get a knife and cut off the top of your pineapple. Working your way around and leaving about a ¾-inch border, cut down and around and inside the "skin" of the pineapple. You're trying to keep it intact as best you can while you basically scoop out the flesh of the fruit. Use a spoon. Get down as far as you can. You want about 1 ½ cups of pineapple. Cut it into chunks.
3. Light a grill (or just heat a medium skillet over medium-high). Add the pineapple to the skillet and throw it on the grill (or the stovetop) and cook it,, stirring occasionally, until it gets nice and caramelized, about 15 minutes. Take it off the heat and let it cool down.
4. Throw your cooked pineapple into a blender with the rum, coconut milk, and lime juice. Add a bunch of ice, probably around 2 cups or so, and purée it until smooth. Pour it into the pineapple shell, add some pretty garnishes to make it fun and you feel fancy, and drink it through a straw.