Slice off the leafy top and bottom of the pineapple. Stand it upright and trim away the outer peel. Slice into eight thick rounds and remove the core from each slice using a pineapple corer or a small round cutter or knife. Reserve ⅓ cup (80 ml) of the fresh juice. Make sure you are slicing and coring the pineapple in a way that you can capture the juice as it comes out of the pineapple.
1 whole (~3.3 lbs / 1.5 kg) fresh pineapple, ⅓ cup (80 ml) fresh pineapple juice
In a large bowl, whisk together the dark brown sugar, cinnamon, sea salt, vanilla extract, dark rum, and reserved pineapple juice until the sugar is mostly dissolved. Add the pineapple rings and turn to coat evenly. Marinate for 15 minutes, flipping halfway through.
½ cup (110 g) packed dark brown sugar, ½ tsp (1 g) ground cinnamon, 1 tsp (6 g) sea salt, 1 tsp (5 ml) vanilla extract, ⅓ cup dark rum
Heat a cast iron grill pan over medium-high heat. Add the ghee and swirl to coat the ridges evenly. Remove the pineapple from the marinade, allowing excess liquid to drip off, and reserve the marinade. Arrange the rings in a single layer on the grill pan. Cook for 3 to 4 minutes per side, or until distinct grill marks form and the fruit is lightly caramelized. Transfer to a plate.
1 tbsp (14 g) ghee
Place the butter in a small saucepan over medium heat. Add the reserved marinade and bring to a gentle simmer. Cook, stirring occasionally, until reduced to a thick, glossy syrup, about 5 to 7 minutes. Remove from the heat.
4 tbsps (56 g) unsalted butter
To assemble, place one warm pineapple ring in a serving bowl. Top with a scoop of vanilla ice cream. Add a second pineapple ring and another scoop of ice cream. Spoon the warm buttered rum sauce over the top. Finish with whipped cream and a maraschino cherry. Crumble waffle cone shards over the top if you like. Serve immediately.
4 cups (480 g) vanilla ice cream, 1 cup (60 g) whipped cream, 4 maraschino cherries