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Cut the pineapple into spears, removing the skin and core. Place the pineapple spears in a zip-top bag with Mazola Corn Oil, sugar and 2 tablespoons rum. Toss well to coat. Let rest at least 15 minutes to allow the pineapple to absorb the flavors.
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Heat the grill to medium-high heat. Place the spears on the grill and grill for 5 minutes, turning occasionally, until all sides are caramelized. Freeze for at least 15 minutes.
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From the grilled spears, cut six narrow spears for garnish.
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Place the remaining grilled spears in a blender and blend until smooth. Add 1 cup rum, coconut water and half and half. Add the ice and blend until smooth.
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Pour into a glass and garnish with a pineapple spear.