Using an electric mixer or by hand using a whisk, beat the cream and vanilla in a bowl until stiff peaks form. Refrigerate.
Prep the banana per the instructions above.
Add the banana, chocolate syrup, yogurt, and milk to a blender. Blend until smooth. Taste and adjust any of the ingredients as needed for flavor, add more milk for consistency or volume.
To serve: Transfer the smoothie to a glass or to-go cup. Top with whipped cream and cacao nibs.