For the cupcakes: Preheat the oven to 350 degrees F. Line a standard muffin pan with 12 cupcake liners.
In the bowl of an electric mixer fitted with the paddle attachment, combine the butter and granulated sugar. Cream on high speed until the butter is light and fluffy, about 6 minutes. Sift together the flour, baking powder and salt. Set aside.
Combine the coconut milk, whole eggs, egg whites and vanilla extract. Alternately add the flour mixture and the coconut milk mixture to the creamed butter in three stages, allowing the batter to mix for 30 seconds after adding the dry or wet ingredients. Fold in the desiccated coconut. Fill the cupcake liners three-quarters full with batter and bake until golden brown and baked through, about 25 minutes.
For the dark rum syrup: Bring the granulated sugar and 1 ounce water to a gentle simmer. Remove from the heat and stir in the dark rum. Liberally douse the baked cupcakes with syrup immediately upon removing the cupcakes from the oven. Cool the cupcakes completely.
For the pineapple filling: Preheat the oven to 350 degrees F. Sprinkle the brown sugar into the bottom of an 8-inch square baking dish. Drizzle the honey and sprinkle the cinnamon on top of the brown sugar. Peel, core and small dice the pineapple. Evenly distribute the pineapple over the brown sugar. Wrap the baking dish with aluminum foil and bake for 15 minutes. Remove from the oven, remove the foil and stir the pineapple and liquefied sugar. Replace the foil and bake the pineapple for another 15 minutes. Remove from the oven, remove the foil and stir the pineapple and liquefied sugar. Bake the pineapple, uncovered, for another 15 minutes. Remove from the oven and allow to cool completely.
For the tangelo cream cheese icing: In the bowl of an electric mixer fitted with a paddle, beat the butter until light and fluffy on medium-high speed. Add the cream cheese and mix on medium-high speed until well combined and lump free. Scrape down the sides of the mixer bowl and add the powdered sugar. Stir on low speed until well combined. Add the vanilla extract and tangelo paste and beat on medium-high speed for 2 minutes. Place in a pastry bag fitted with a large round tip.
To assemble: Using an apple corer, remove the center core of the baked cupcakes and fill with oven roasted pineapple. Pipe tangelo cream cheese icing generously on top of the cupcakes. Roll the cupcake icing in toasted desiccated coconut, and garnish with a mandarin orange segment and rolled fondant street sign.
This recipe was created by a contestant during a cooking competition. It has not been tested for home use.
Recipe courtesy Casey Shiller, Jilly's Cupcake Bar and Cafe