Combine granulated sugar, 3 tablespoons bourbon, 3 tablespoons water, and juice in a medium saucepan over medium-high heat; cook 2 minutes or until sugar dissolves, stirring constantly. Bring to a boil; reduce heat to medium and cook, without stirring, 10 minutes or until golden. Remove from heat. Carefully add cream, stirring constantly (mixture will bubble vigorously). Cool slightly. Stir in remaining 2 teaspoons bourbon and vanilla.
Preheat broiler to high.
Cut pineapple lengthwise into 12 slices; cut each slice in half crosswise. Arrange pineapple on a foil-lined broiler pan coated with cooking spray; sprinkle evenly with brown sugar. Broil 5 inches from heat for 12 minutes or until golden brown.
Scoop 1/3 cup ice cream into each of 6 bowls. Arrange 4 pineapple slices in each bowl; top each serving with 2 1/2 tablespoons caramel sauce. Sprinkle each serving with 2 teaspoons coconut; serve immediately.
My husband made this for me as a date night treat. The space from the broiler might be important because ours turned out perfectly. The bourbon sauce is divine and I admit that it was used on many a bowl of ice cream afterwards.
I was really disappointed with the overall outcome of this recipe. The pineapple and brown sugar smoked up my oven to a good extent. I ended up throwing away the pineapple because it just didn't taste good. I will say, however, that the bourbon sauce and toasted coconut started a little bit of an ice cream topper addiction. The sauce/coconut combination is divine.
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