Wash the strawberries very well and remove any green parts, slice into small pieces.
Keep aside a few pieces of fresh strawberries aside for garnishing (about 2 tablespoons chopped strawberries).
Transfer the remaining chopped strawberries to a good quality medium sized saucepan.
Add the sugar, mix well with the strawberries.
As the sugar begins to dissolve, cook the mixture in medium for few minutes, about 3 to 4 minutes until the strawberries are cooked and soft and the juice is released.
Once the strawberries are cooked, switch off the stove, and mash the cooked strawberries (a potato masher works well) to make the strawberry syrup.
You do not need to mash this a lot, as few small chunks of strawberries are good for strawberry milk.
If you prefer this to be smooth, you can mash it really well or even puree the contents if you wish.
When it's ready, add the milk and vanilla, mix well to combine with the strawberry syrup that we prepared.
Once the milk is mixed well with the strawberries, allow the strawberry milk mixture to completely cool down.
When the mixture is cooled to room temperature, transfer the prepared milk to glass bottle or jar and chill the milk in the refrigerator.
If you wish a smooth consistency for the drink, you can also blend the contents using a hand mixer or using a blender! I like the texture of strawberries in this drink, but you can blend it for a smoother more easy to drink texture like a milkshake, if you want to.
Once the strawberry milk is chilled, transfer the milk to serving glass cups, garnish with sliced, fresh strawberries (that we kept aside early), and serve!
Make sure to keep the strawberry milk refrigerated and always serve it chilled for best results!