Combine the milk, cream and chocolate in a medium saucepan over medium heat and cook until simmering; whisking until the chocolate melts and the mixture is smooth.
Add the vanilla and espresso and whisk until incorporated. Just bring to a boil and turn off heat.
Add the Amaretto and whisk in. Remove 1/4 cup of mixture and allow to cool. Keep hot chocolate covered on low heat.
Whip cream on high until soft peaks form. Add powdered sugar and chocolate mixture and mix thoroughly. Continue beating until stiff peaks form.
Fill mugs just above halfway with hot chocolate and top with whipped cream.