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

Pineapple Whiskey Upside Down Cakes

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

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

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 in this one I’m using vanilla whiskey, 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.

On our trip to St. john back in November, we made Pineapple Upside Down Shots for one of the happy hours that took place on our balcony. More to come on that recipe soon…but this is what they looked like.

They were a big hit at happy hour that night, even some non whiskey drinkers seemed to really like them. So what I thought about doing is turning that shot into a dessert

So I decided to make this recipe in a jumbo muffin pan to make them an individual dessert, but you could take the same recipe and put it in a regular cake pan if you want to make the whole thing and cut it up.

Place a slice of pineapple and a cherry in each muffin tin.

Make the batter using a boxed yellow cake mix (keeping it easy here) along with the juice from the pineapple can and yes – the vanilla whiskey.

One of my new favorite flavored whiskeys to drink is Crown Royal Vanilla. It just hit the shelves a few months ago and I was actually lucky enough to go to the launch party. I liked it the first time I tried it and the rest is history.

And vanilla, right? You use vanilla when you bake…so it makes perfect sense to me.

Pour the batter on top of the pineapple and cherry and get it in the oven.

When they come out of the oven give them about 5 minutes to cool and then flip them out. Don’t let the cakes sit in the muffin pan for too much longer or they’ll get stuck to the pan.

Perfect dessert to go with the perfect shot!

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


These Pineapple Whiskey Upside Down Cakes are best served the day you make them, but I’ll tell you, no one complained about eating the few that were leftover the next day!


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

Pineapple Whiskey Upside Down Cakes

  • Author: Dan
  • Yield: 12 1x


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


  1. heat the oven to 350 degrees.
  2. Place a teaspoon of butter into each jumbo muffin tin.
  3. Next 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 up to 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 to remove the cakes.
  8. Cakes are best served warm.


3 Responses

  1. 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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