Add the cherries, 3 tablespoons of sugar and 1 tablespoon of the Amaretto to a medium mixing bowl. Gently toss the cherries and let macerate for 15-20 minutes.
Transfer the cherry mixture to a medium saucepan. Cook for 8-10 minutes over medium heat until the cherries have broken down and are softened, stirring occasionally. Set aside and allow to cool at room temperature.
Add the coconut milk, remaining 1/2 cup sugar, salt, remaining 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.
Pour half of the cherry mixture into the Dixie cups and freeze for another 30 minutes.
Pour the chilled Amaretto cream mixture into a blender or food processor and purée.
Add a layer of the amaretto cream mixture and freeze for another 30 minutes.
Fill the rest of each Dixie cup with the remaining cherry mixture and freeze for 1-1/2 hours.
Insert a wooden craft stick into each Dixie cup and freeze overnight.
Before serving, cut a small slit at the top of each cup to help loosen them and unwrap.
NOTE: To make a kid-friendly version, substitute your favorite fruit juice for the Amaretto.