In a small bowl, mix together the cherries, Amaretto, and sugar. Allow the mixture to rest for 30 minutes, giving it a gentle stir now and then.
In a large mixing bowl, blend the mascarpone cheese, powdered sugar, and vanilla extract until the mixture is smooth and creamy.
In another bowl, whip the heavy cream until it forms stiff peaks, then carefully fold it into the mascarpone mixture to keep the texture light and airy.
Quickly dip each ladyfinger into the cooled espresso and arrange them in a single layer at the bottom of your serving dish.
Spoon half of the mascarpone mixture over the ladyfingers and spread it evenly.
Spoon half of the cherry mixture on top of the cream layer.
Repeat the layers with the remaining espresso-dipped ladyfingers, mascarpone cream, and cherries.
Finish by dusting the top with cocoa powder and, if you like, some shaved dark chocolate for garnish.
Cover and chill in the refrigerator for at least 4 hours before serving to allow the flavors to meld and the dessert to set.