Pineapple Upside Down Shots

Pineapple upside down shots taste exactly how you’d think! They’re all the flavor of a pineapple upside down cake, but in drinkable, alcoholic form. With a smooth, sweet, fruity flavor, and a strong kick from vanilla whiskey, these shots go down easily, while giving you a nice buzz. 

Two pineapple upside down shots surrounded by pieces of pineapple upside down cake, with a bowl of pineapples and maraschino cherries in the background

A Fun Party Shot Favorite 

If it wasn’t clear from my pineapple upside down whiskey cakes, I’m a pretty big fan of adding whiskey to the classic, mouth-watering flavor of pineapple upside down cake. Whiskey and pineapple complement each other perfectly, and these party shots are a shining example of that.

One of the secrets of this recipe is vanilla whiskey, which pairs brilliantly with pineapple juice and maraschino cherries. The result is a well-balanced gulp of boozy dessert that isn’t overly sweet. You’ll be amazed at how much these taste like the actual cake.

I love to make a tray of these for a party, and watch them disappear in minutes. They’re that popular!

A tray full of pineapple upside down shots on the beach, with water and boats in the background

Ingredients For Pineapple Upside Down Shots

There are only four ingredients in these shots, so they’re as easy to make as they are fun to drink. Make sure you scroll to the recipe card at the bottom of the article for the exact quantities.

  • Crown Royal vanilla whiskey – You can use any brand of vanilla whiskey, but I prefer Crown Royal.
  • Pineapple juice
  • Cake vodka
  • Maraschino cherries 

What is Cake Vodka?

Cake vodka is just vodka that is cake flavored. Different brands have slightly different flavors, but most taste like a generic white cake.

How to Make Pineapple Upside Down Shots

This recipe only takes a few minutes to make. That’s a very good thing, because chances are you’ll have to make a second – or third! – batch if you serve these at a party. 

  • Add the cherries. Start by placing a maraschino cherry in the bottom of each glass.
  • Fill the shaker. Add the pineapple juice, vanilla whiskey, and cake vodka to a cocktail strainer, then add ice.
  • Shake and serve. Shake the pineapple upside down shots, then pour them into the shot glasses. Time to drink! 
Two pineapple upside down shots next to a slice of pineapple upside down cake, a bottle of Crown Royal vanilla whiskey, and a down of pineapple slices and maraschino cherries

Tips for Success

These pineapple upside down shots are one of my favorite sweet treats for a boozy party. But there are a few things you can do to make sure that they end up perfect. 

  • Chill the shot glasses. For best results, place the glasses in the freezer for at least an hour before making these shots. That way these tangy shots will stay cold when you serve them.
  • Don’t over shake. The ingredients in this recipe will mix together easily. The purpose of shaking the shot is just to make the drink cold before you pour it into the glass. Don’t shake it for too long, or some of the ice will melt and start to dilute the mouth-watering shots. 
  • Use good quality ingredients. This is a shot, so it’s not the time to be using $100 vodka. But you’ll still get much better results if you use good quality alcohol and pineapple juice. 
Two pineapple upside down shots next to a few slices of pineapple upside down cake, with a bowl of pineapple slices and maraschino cherries in the background

Can Pineapple Upside Down Shots Be Made Ahead of Time? 

These shots don’t need to be consumed as soon as they’re made, but the ingredients will start to separate if they’re left to sit for many hours or days. If you want to make these shots ahead of time, mix the ingredients together, but don’t pour the shots. Then, when you’re ready to serve them, add the mixture to the cocktail shaker, shake them with ice, and serve them fresh.

Looking For More Shot Recipes?

These aren’t the only shots that I love to serve at parties! If you want some more options, check out some of my other favorites.

These Pineapple Upside Down Shots taste just like the dessert!

Pineapple Upside Down Shots

  • Author: Dan
  • Prep Time: 4 minutes
  • Cook Time: 0 minutes
  • Total Time: 4 minutes
  • Yield: 4 1x

These pineapple apple down shots are a classic dessert in a shot glass. With tangy pineapple, cake vodka, and smooth vanilla whiskey, these will be a hit at your party.



  • 4 ounces Crown Royal Vanilla Whisky
  • 2 ounces pineapple juice
  • 2 ounces Cake Vodka
  • 4 maraschino cherries


  1. Add a cherry to the bottom of each glass.
  2. Add the ingredients to a cocktail shaker filled with ice.
  3. Shake well and strain into 4 tall shot glasses.
  • Category: Shots
  • Method: Pour
  • Cuisine: American

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