Hand mix the whipped cream and cheeses until blended.
Add vanilla, Luxardo Amaro, and almond extract. Transfer mixture to a large stand mixer. Using a mixing paddle on low speed, slowly add cherries, and blend until mostly puréed.
Remove the bowl from the stand mixer, and add the cocoa chips, hand mixing until well incorporated.
Fill a piping bag with the mixture, and begin filling cannoli shells from both sides. Repeat until finished, and garnish with confectioners’ sugar and cocoa chips.