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Slice the pineapple into ¾- to 1-inch-thick rounds with the rind still on. Remove the core from each round using a small ring cutter (about 1 inch). Cut each round into 8 wedges. (Alternatively, cut each round into 8 wedges and then trim the core from each piece.) Place the wedges in a 3-quart baking dish and poke them all over with a toothpick.
Stir together the coconut rum, dark rum and cream of coconut in a large measuring cup. Pour the rum mixture over the top of the pineapple wedges and refrigerate for at least 6 hours and up to overnight.
Preheat the oven to 325 degrees F.
Place the coconut on a small baking sheet and bake, stirring halfway through, until toasted, about 12 minutes. Transfer to a shallow bowl and let cool.
Drain the rum mixture and save to turn into a beverage. Roll the pineapple wedges in the toasted coconut and place on a serving platter. Top each wedge with a maraschino cherry followed by a cocktail umbrella toothpick on a slight angle to secure the cherry.