01 - Add vanilla ice cream, whole milk, peppermint extract, fresh mint leaves if using, and granulated sugar to blender canister.
02 - Process on high speed until mixture reaches completely smooth, creamy consistency without visible mint leaf pieces.
03 - Taste milkshake and modify sweetness level or mint intensity by adding small amounts of sugar or extract as needed.
04 - Divide blended milkshake evenly between two chilled serving glasses.
05 - Top each glass with generous swirl of whipped cream and place one maraschino cherry on peak.
06 - Present immediately accompanied by drinking straws while maintaining optimal chilled temperature.