I kicked off summer making pineapple milkshakes, boos, and I’m gonna be sippin’ on them all season long! Didn’t think I could get a pineapple milkshake this creamy, but turns out pineapple sherbet, crushed pineapples, and vanilla ice cream together really do something. And the flavor, y’all! It’s like drinking a pineapple upside-down cake. Get into it.
This post may contain affiliate links. Read our disclosure policy.

How to Make Pineapple Milkshakes
Step 1: Add all the ingredients into the steel mixing cup of your drink mixer. Blend until smooth, adjusting with more milk if you want it thinner.
Step 2: Pour your pineapple milkshake into glasses and top with your favorite garnishes! Fresh whipped cream, cake crumbles, chopped pineapple, caramel sauce, cherries, etc.
Pineapple Milkshake Recipe
Want to Save This Recipe, Boo?
Equipment
Ingredients
- 1 cup vanilla ice cream
- ½ cup pineapple sherbet
- ¼ cup crushed pineapple
- ½-1 cup milk ½ cup if you prefer thick shakes and 1 cup if you like them thinner
- 1 pinch ground cinnamon
- 1 tablespoon caramel sauce
- Optional: Garnish with fresh whipped cream, cake crumbles, chopped pineapple, caramel sauce and/or cherries
Instructions
- Add vanilla ice cream, pineapple sherbet, crushed pineapple, milk, ground cinnamon and caramel sauce into the steel mixing cup of your drink mixer and process until smooth and blended to your preference. Add more milk if you prefer milkshakes a bit thinner.
- Pour milkshake into two glasses and garnish with toppings of your liking.
Notes
- Use good ice cream, boos. This pineapple upside down milkshake starts with real-deal, creamy vanilla. None of that fake stuff!
- Chill your glasses before pouring. A cold glass keeps your shake thick and frosty longer.
- Start blending slow, then go high. It helps keep the texture creamy without turning your shake into soup.
- Adjust your milk. If you love a thick and creamy milkshake, use a bit less milk. But if you want it more sippable, then add more milk.
- Straw and spoon. Serve it up with both to sip and scoop as desired! A spoon comes in handy to enjoy the cake and pineapple tidbits in the topping along with the creamy cold pineapple shake in each bite.
Nutrition
Recipe Help
Yup! You can use a regular blender if you think it can take it. A food processor works great too! You’ll just need to add a little more milk to help it blend. This pineapple shake is on the thick side.
Add more ice cream or sherbet. Start with a couple spoonfuls and blend again until it’s as thick as you want.
More Drink Recipes
- Banana Milkshakes
- Oreo Milkshakes
- Strawberry Float
- Southern Iced Sweet Tea
- New Orleans Hurricane Drink
- Sweet Peach Tea
Want to Save This Recipe, Boo?
This Over The Top Pineapple Milkshake looks absolutely incredible! I love how you’ve combined such vibrant flavors. Can’t wait to try this recipe and impress my friends at the next get-together!
holy moly Jocelyn I could really go for one of these right about now 🙂
Oh man this looks amazing! Can we just call it a “smoothie” so I can go ahead and have it for breakfast?! Please.
You transformed a pineapple upside down cake into a MILKSHAKE!????????!!!!!!!! <3 <3 <3 GENIUS!!!!!!!!! *_* ^_^ I.WANT!
Thanks so much my dear! These are seriously so delish!
Oh yum pineapple is one of my favorite summer fruits. Heading over to check out the full recipe now!
Do you have a preference on posts like this to pin to your site or theirs?
Hey hon, either is fine my dear! Thanks so much!