In a medium saucepan dissolve sugar in the coffee. Bring mixture to a light boil then reduce to simmer. Simmer until the mixture has reduced to form a slightly thickened syrup, about 15 minutes. Remove from heat and whisk in vanilla extract. Cover and refrigerate until very cold.
In a blender add the ice cream, milk, chilled coffee syrup and the Kahula. Blend until smooth. Top with whipped cream and a few chocolate covered coffee beans.