Fresh Strawberry Milkshakes

In a mixing bowl combine the sliced strawberries, sugar and vanilla extract and stir to combine well. Set aside and allow to macerate for at least 20 minutes and up to 1 hour.
In a large mixer, place the strawberries, ice cream, and milk. Blend until smooth. Pour into ice cream parlor glasses and garnish the rim of each glass with whole strawberries. Serve immediately.