Pineapple Upside Down Whiskey Cakes

Pineapple Upside Down Whiskey Cakes are just like the original, but with a boozy kick! A splash of vanilla whiskey makes this classic dessert even better!

Love boozy desserts? Try our Banana Bourbon Poke Cake or this Bourbon Cherry Pie!

Pineapple Upside Down Whiskey Cakes is a dessert recipe for parties

Boozy Dessert Recipes

You know I can’t just leave well enough alone.

I find a recipe I like, and add my own twist to it. Sometimes with booze, sometimes without – but the Pineapple Upside Down Whiskey Cakes were screaming for some whiskey.

Vanilla whiskey, that is. And I think you’re going to love it.

I’m a big fan of the boozy dessert as you know by now. Why not keep the party going at dessert time, right? I love serving things like this boozy Bananas Foster or these Coconut Rum Cookies. Just a little bit of booze baked in to your dessert…it’s the perfect ending to a party.

After adding the whiskey, I also decided to make this recipe in a muffin pan to make them individual desserts. But you can also use this same recipe and put it in a regular cake pan if you want to make a whole cake.

How To Make Individual Pineapple Upside Down Cake

Start by adding butter and brown sugar to the bottom of each muffin tin. Next place a slice of pineapple and a cherry into each muffin tin, on top of the butter and brown sugar.

Prepare the cake batter according to the package directions along with the juice from the pineapple can and the vanilla whiskey.

Crown Royal Vanilla Whiskey was the perfect booze for these pineapple upside down cakes. I mean, vanilla, right? There’s usually vanilla extract in cake recipes so it made sense to me.

Now pour the batter on top of the pineapple and cherries and place into the oven to bake.

When they come out of the oven give them only about 5 minutes to cool and then flip them out. Don’t let these boozy cakes sit in the muffin pan for too long or they’ll stick to the pan.

Can You make This Cake Recipe Ahead Of Time?

These pineapple upside down cakes are better when they are first made, but you can make them ahead of time too.

All you need to do is warm them up in the microwave for about 30-45 seconds until they warm through and the brown sugar melts again. Eat as is or top with vanilla ice cream!

And maybe a shot of whiskey on the side!

Pineapple Whiskey Upside Down Cakes are a fun, boozy dessert!



Pineapple Upside Down Whiskey Cakes collage for Pinterest

Looking For More Easy Dessert Recipes?

Pineapple Whiskey Upside Down Cakes are a boozy version on the classic dessert!

Pineapple Upside Down Whiskey Cakes

  • Author: Dan
  • Prep Time: 10 minutes
  • Cook Time: 30 minutes
  • Total Time: 40 minutes
  • Yield: 12 1x

This boozy pineapple dessert is perfect for parties! Individual cakes make party planning a breeze!



  • 1 box yellow cake mix
  • 1/4 cup butter, melted
  • 3/4 cup brown sugar
  • 3 (8 oz.) cans of sliced pineapple in juice (drained reserving 1/2 cup of the juice)
  • 12 maraschino cherries
  • 1/2 cup Crown Royal Vanilla Whisky
  • 1/2 cup vegetable oil
  • 3 eggs


  1. Preheat the oven to 350 degrees.
  2. Place a teaspoon of butter into each jumbo muffin tin.
  3. Add a tablespoon of brown sugar to each muffin tin, then top with a pineapple slice and a cherry in the center.
  4. Mix the cake batter with the whiskey, pineapple juice, eggs and oil with a hand mixer on low speed until all the ingredients are combined.
  5. Turn the mixer on high and blend for an additional 2 minutes.
  6. Divide the batter between the 12 muffin tins and place in the oven for 30 minutes.
  7. Cool the cakes for 5 minutes then turn over on a sheet pan or cutting board to remove the cakes.
  8. Best served warm, or store and heat up in the microwave for 30 seconds before serving.
  • Category: Dessert
  • Method: Oven
  • Cuisine: American


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8 Responses
  1. Monique

    When I saw this recipe in my Feedly feed, I started doing a happy dance. I love, love, LOVE boozy pineapples. Actually I’m partial to all tropical-ish boozy desserts. I tweeted about your Coconut Rum Cookies a couple of days ago and apparently my followers are on the boozy tropical dessert kick too. (It got a lot of feedback!)

    I have to get my hands on some Vanilla Crown Royal this weekend so I can try this recipe.

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