Rinse the cherries thoroughly under cold water and pat them dry with paper towels. Remove the pits and stems—I find using a cherry pitter makes this quick work, but a small knife works too. Set the prepped cherries aside. Dry cherries blend more smoothly and won't dilute your shake with excess water.

Add the prepared cherries, yogurt, almond milk, sweetener, vanilla extract, and salt to your blender. Blend on high speed for 60-90 seconds until completely smooth and creamy. I like to start on medium speed for a few seconds to break down the cherries, then increase to high for a silkier texture—this prevents the blender from working too hard upfront.

Pour the milkshake into chilled glasses and top with fresh cherries and chocolate chips as desired. Serve immediately while the shake is cold and thick.