In a blender, combine the vanilla ice cream, whole milk, peppermint chocolate syrup, and vanilla extract.
Blend on medium speed until smooth and creamy, about 30 seconds to 1 minute. If the milkshake is too thick, add a little more milk until you reach your desired consistency.
Taste the milkshake and adjust the sweetness if necessary by adding a little extra peppermint chocolate syrup. Blend again briefly to mix.
Pour the milkshake into tall glasses.
Top generously with whipped cream, letting it spill over the edges slightly for a festive touch.
Sprinkle crushed candy canes and cocoa powder on top of the whipped cream for a delightful festive crunch.
Finish with a maraschino cherry on each glass as the cherry on top!
Notes
Adjust the sweetness by adding more syrup if desired.