In a medium saucepan over medium heat, combine 2 cups of pitted fresh cherries, 1/4 cup granulated sugar, 1 tablespoon lemon juice, and 1/4 cup Amaretto. Cook for 5–7 minutes, stirring occasionally until the cherries soften and the mixture becomes syrupy. Once done, remove from heat and allow it to cool completely.

In a large mixing bowl, use an electric mixer to beat 1 cup of cold heavy cream until soft peaks form, about 3-5 minutes on medium speed. In another bowl, whisk together 1 cup mascarpone cheese, 1/2 cup powdered sugar, and 1 teaspoon vanilla extract until smooth and creamy. Gently fold the whipped cream into the mascarpone mixture until well combined and fluffy.

Prepare a cup of strong espresso or brewed coffee and let it cool slightly. Stir in 2 tablespoons of Amaretto into the cooled espresso, mixing well. Pour this mixture into a shallow dish for assembling the tiramisu.

Quickly dip each ladyfinger into the espresso mixture, ensuring they are soaked but not soggy (2-3 seconds per side). Begin layering your Cherry Amaretto Tiramisu starting with a layer of dipped ladyfingers, followed by half of the mascarpone cream, and half of the cherry mixture. Repeat the layers, finishing with the remaining mascarpone and cherries on top.

Once assembled, cover the dish tightly with plastic wrap and refrigerate for at least 4 hours, ideally overnight. This chilling time allows the flavors to meld and gives the dessert a firmer texture.

Before serving, remove from the refrigerator. Dust the top generously with cocoa powder, and for an extra touch, add shaved chocolate and fresh cherries for garnish. Slice into portions and serve chilled.