It's easy to make pineapple milkshakes at home Just combined roasted cinnamon pineapple, vanilla ice cream, and whole milk in a blender and mix together!
Spray a medium-sized baking dish with cooking spray.
Cut pineapple into bite-size chunks. Arrange pineapple in a single layer in the prepared baking dish.
Sprinkle the pineapple with brown sugar and cinnamon, then stir ingredients together until the pineapple is fully coated.
Roast the pineapple at 425F for 20-25 minutes, until pineapple has softened and become a little gooey.
ROASTED PINEAPPLE MILKSHAKE INSTRUCTIONS
Add ¼ cup milk and the roasted pineapple, along with any pineapple drippings from the baking dish, into a blender.
Cover the blender and pulse the mixture 2-3 times to combine the pineapple and the milk.
Add 2 cups of vanilla ice cream to the blender. Then cover and pulse 2-3 times to combine all ingredients.
Check the milkshake consistency with a spoon. Add more milk if you want at thinner milkshake; add more ice cream if you want a thicker milkshake. Pulse a few times after adding more of any ingredient.
Pour Roasted Pineapple Milkshake into a 15-oz glass (or two smaller glasses) and serve immediately. If desired, garnish with a whipped cream, cherries, nutmeg, and a pineapple chunk.