In a blender, combine the vanilla ice cream, milk, cocoa powder, instant coffee, and peppermint extract. Tip: For a stronger coffee flavor, use espresso powder instead of instant coffee.

Blend on high speed until smooth and creamy, about 30 seconds. Tip: If the shake is too thick, add a splash more milk.

Drizzle chocolate syrup inside two tall glasses, then pour the milkshake into the glasses. Tip: Swirl the chocolate syrup up the sides for a pretty presentation.

Top with whipped cream and crushed candy canes. Tip: For extra indulgence, add a drizzle of extra chocolate syrup.