Place the cookies on the bottom of a cake pan, creating a base for the tiramisu. Splash 1/2 cup Vin Santo over the cookies and set aside. Cook's Note: The exterior of the cookie should be wet while the interior should remain somewhat dry.
In a bowl, add the mascarpone, chocolate, sugar, and remaining 1/2 cup Vin Santo. Whisk the ingredients together until creamy and thoroughly mixed.
Spread the cream mixture evenly over the cookies, making sure all the cookies are completely covered. Cook's Note: If you like, you may also sprinkle the top of the tiramisu with additional chopped chocolate and cookies.
Unlike traditional tiramisu, this version can be served immediately.