Using a standing mixer fitted with the whisk attachment or an electric mixer, whip the heavy cream until stiff peaks form.
Meanwhile, in a medium bowl, combine ricotta, powdered sugar, and 2 teaspoons vanilla. Fold in whipped cream, cover, and refrigerate while making the Pizzelle cookies.
To make the Pizzelle cookies:
Preheat Pizzelle iron and lightly coat with nonstick cooking spray.
In a large bowl, combine flour, sugar, butter, eggs, vanilla, and baking powder. Drop slightly rounded tablespoons of batter on to Pizzelle iron and close. Bake as directed by manufacturer or until golden brown, 30 seconds to 1 minute.
Using a nonstick spatula, remove one pizzelle, leaving the second still on the open press, carefully wrap around a ¾” wooden dowel and pinch where the ends of the cookie meet. Hold until pizzelle is cool enough to retain its shape, using a kitchen towel if necessary to prevent burning your fingers. Repeat with second cookie on press and all remaining batter.
To assemble the mock cannoli:
Remove filling from the refrigerator and fold in chocolate chips. Using a pastry bag fitted with only a large coupler and no tip, pipe the filling into each side of a cooled pizzelle. It is okay if the filling does not go all the way through the middle of the cookie.
Garnish with additional chocolate chips and dust with powdered sugar if desired. Serve immediately or chill until serving time.
Pizzelle iron: Modern versions are just like a waffle maker: a silvery, shiny, beautiful waffle maker that makes cookies. I have this pizzelle iron (Culinary Hill may earn money if you buy through this link).
Vanilla extract: Or substitute anise or almond extract. For lemon, use 1 teaspoon lemon oil instead of lemon extract (lemon extract doesn’t have enough flavor).
Yield: This recipe about 36 cannoli (12 servings of 3 cannoli per person). The recipe may be halved.
Make ahead: The prepared cannoli shells will keep, unfilled, up to two weeks if stored in an airtight container in a cool, dry place. Unfortunately the shells cannot be filled in advance because the ricotta cheese filling will make the cannoli soggy.
Finishing touches: Sprinkle the ends of the cannoli with tiny chocolate chips, chopped pistachios, chocolate shavings, or finely chopped candied orange peel. Finally, give the outside a dusting of powdered sugar.