Tropical Vibes: Pineapple Upside-Down Cake Cocktail
I’m back! It has been a weirdly long time since I shared a cocktail recipe. I’ve just been in a kind of cocktail slump. But get ready, there are a bunch comin’ at ya…
Beginning with this DELICIOUS pineapple upside-down cake cocktail.

The flavor of this tropical-ish cocktail is definitely pineapple-forward, mellowed by warm spices and brightened by tart lime. It’s deliciously complex, but oh-so-easy to whip up.
It’s giving off a strong tiki feel, which is pretty on-trend as well. All it needs is a pineapple leaf or palm frond.
Making this is craaaaazzzzyyy easy. Just fill a shaker halfway with ice and add all the ingredients (except garnishes). Shake for around 20 seconds.

Strain into a coupe glass and garnish. You could go a number of different directions with garnishes.
I had dehydrated blood orange slices on hand, so tried that. I like the idea of a bourbon cherry (very “pineapple upside-down cake”). And I really wanted to do a charred pineapple wedge, but didn’t have a fresh pineapple on me.
I have yet to make a truly awesome pineapple upside-down cake (like, the actual cake), but I feel like I’ve cracked the code on the cocktail version.

I’ve got some other great pineapple drinks coming your way, but this cake-themed cocktail is going to be hard to top!
Other tropical-ish drinks you’ll love:
- Spiced Banana Daquiri Cocktail (Not Frozen)
- Fuzzy Navel All-Grown-Up (Mint & Apricot Gin Cocktail)
- “Trouble In Paradise”: Spiced Peach Bourbon Cocktail
- “Mayan Sour” (Spiced Banana Whiskey Sour)
- Berry-Basil Smash (A Refreshing Gin Cocktail)
- Bohemian Cocktail (Gin, Elderflower, & Grapefruit)
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Pineapple Upside-Down Cake Cocktail
You didn't know you needed a pineapple upside-down cake cocktail in your life, but you just didn't know what you were missing! This easy and delicious drink uses a good dark rum, pineapple juice, and warm cinnamon syrup with a hit of tart lime that brings a tropical vibe in even the coldest weather!
Ingredients
- 1 1/2 ounces of dark rum
- 1 1/2 ounces of pineapple juice (100%, no sugar added)
- 3/4 ounce of cinnamon simple syrup (see notes)
- 3/4 ounce of fresh lime juice
- Dust of cinnamon
- Optional: charred pineapple and/or bourbon cherry garnish
Instructions
- Fill a shaker halfway with ice and add all the ingredients (except garnish).
- Shake for around 20 seconds.
- Strain into a coupe glass and garnish. Enjoy!
Notes
- Making a cinnamon simple syrup is super easy. Just stir together equal parts sugar and water in a saucepan (1/2 cup of each is fine unless you have a crowd). Heat on medium until it is at a strong simmer, ready to boil. Remove from heat and add a couple cinnamon sticks. Stir and let steep for 10 minutes, then remove the cinnamon. Will keep in the fridge for a couple weeks.
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