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Add the cherries, 3 Tablespoons of sugar and 1 Tablespoon Amaretto to a medium mixing bowl. Gently toss to coat and let stand for 20 minutes to draw the juice out of the cherries.
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Transfer cherries to a medium saucepan. Stirring occasionally, cook for 8-10 minutes over medium heat until the cherries have broken down and are softened. Set aside and allow to cool at room temperature.
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Add the coconut milk, 1/2 cup sugar, salt, 2 Tablespoons Amaretto and 1 teaspoon almond extract to a medium mixing bowl. Whisk to combine all of the ingredients. Cover and refrigerate for 2 hours.
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Once the cherries have reached room temperature, pour into a blender or food processor and purée. Chill cherry mixture for 30 minutes.
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Once chilled, add 2 Tablespoons of cherry mixture to the bottom of each ice pop mold.
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Add a layer of the Amaretto cream mixture on top of the cherries.
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Repeat with another layer of cherries and top off with the Amaretto cream, up
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to each "fill" line.
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Insert lids with sticks in each mold and press down tightly. Freeze overnight or for at least 6 hours.
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Before serving, run warm water along the bottoms of each mold and gently release.