Prepare strawberries: Hull and chop strawberries. If needed, add sugar and let macerate.
Blend milkshake: Combine strawberries, ice cream, milk, and vanilla extract in a blender. Blend until smooth.
Prepare glass: Drizzle strawberry syrup inside glass.
Pour milkshake: Pour blended mixture into glass.
Garnish: Add whipped cream and optional strawberry garnish.
Serve: Enjoy immediately.
