In a small saucepan over medium heat, combine the raspberries, sugar and water. Bring to a boil, stirring every few minutes, until thickened. Pass the syrup through a mesh strainer and set aside until cooled.
In a blender, combine the milk, vanilla ice cream, raspberry syrup and vanilla extract. Add food coloring for a brighter color pink and blend until smooth. Add food coloring for a brighter color pink. Pour into a glass and top with whipped cream and additional raspberry syrup.