Prepare your glass (optional): Drizzle chocolate syrup around the inside of your serving glass and place it in the freezer to chill while you blend.
Add all ingredients to the blender: Combine the rum, coffee liqueur, crème de cacao, amaretto, milk, vanilla ice cream, and ice.
Blend until smooth: Blend on high speed for about 30–45 seconds until thick and creamy.
Pour and garnish: Remove the glass from the freezer. Pour the Bushwacker into the glass and top with whipped cream and a cherry.
Serve immediately: Enjoy with a straw or spoon!