Drain the Amarena cherries, reserving the syrup. Chop the cherries into smaller pieces, but set aside a few whole ones for garnish.
In a bowl, whisk together the cherry syrup, sweetened condensed milk, powdered sugar, and vanilla extract.
In a large bowl, whip the heavy cream until soft peaks form. Be careful not to overwhip; you want a medium-soft consistency.
Gently fold the whipped cream into the cherry syrup mixture until evenly combined and you have a creamy texture.
Add the chopped Amarena cherries and gently fold them in, distributing them evenly throughout the mixture.
Pour the mixture into an airtight container and place it in the freezer for at least 4-6 hours, or until completely frozen.
Before serving, let the ice cream sit at room temperature for 5 minutes to soften slightly and make it easier to scoop.
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