Pina Colada Popsicles
For Pineapple Layer
1 medium pineapple, peeled, cored and cut into 8 wedges
2 tablespoons (1 oz) + 1 teaspoon rum
6 tablespoons (3 oz) dark brown sugar
For Coconut Layer
1 1/2 cups (12 oz) thai style coconut milk
3/4 cup (2.5 oz) unsweetened shredded coconut
3/4 cup (6 oz) sugar
To make the pineapple layer: Preheat the oven to 425. Line a baking sheet with parchment paper. Place 2 tablespoons of rum and brown sugar in a large bowl and mix to combine. Toss the pineapple in the sugar mixture until well coated. Transfer the the baking sheet and top with any remaining sugar. Bake for 20-25 minutes, stirring well every five minutes, or until the pineapple is starting to brown. It should smell like fragrant caramel at this point. Remove the pineapple from the oven and cool slightly. Transfer the pineapple and any liquid remaining on the baking sheet to a blender and puree until smooth. Add the remaining teaspoon of rum (or more to taste) and blend to combine. Let the mixture cool fully.
To make the coconut layer:
Preheat the oven to 350. Place the coconut on a baking sheet and bake for 5-7 minutes, stirring frequently, or until golden brown. Place the coconut milk and sugar in a small sauce pan. Bring to a boil, stirring frequently to make sure the sugar dissolves. Add the toasted coconut. Remove the pan from the heat and let it steep for 30 minutes. Place a fine mesh strainer over a bowl or measuring cup and strain the coconut milk mixture, pressing down on the solids to extract as much liquid as possible. There should still be approximately 1 1/2 cups. Let the mixture cool completely.
To make the popsicles pour a small amount of the pineapple mixture in the bottom of each mold. Let the first layer freeze completly then add a small amount of the coconut mixture. (If using traditional popsicle molds add the stick when the first layer is partially frozen but still not solid) Let the second layer freeze completely. Repeat until there are five layers, three pineapple and two coconut, or until the mold is full. Freeze until solid.(If using pushpops a good way to keep them upright while freezing is to fill a tall drinking glass with rice and push the pop down into the rice. Place the glass with the rice in the freezer until the pops are frozen.)