Rinse, slice in half and remove pits from cherries. Place on a parchment lined baking sheet and roast in a 400 degree oven for 15-20 minutes. Place cherries in a blender with 2 tablespoons of water and puree. Place puree in a container and refrigerate until cold. Place ice cream, vanilla extract and coconut milk in a blender. Blend until smooth. To serve, divide cherry puree between 3 to 4 glasses. Pour milkshake on top of puree, dividing between the glasses equally.