Roasted Pineapple and Rum Mint Juleps

I do like mixing up my Mint Julep ingredients and these Roasted Pineapple and Rum Mint Juleps veered sharply towards rum but it’s a winner. Thankfully not every horse is the same either!

Roasted Pineapple and Rum Mint Juleps

Yes, you read that right. A Roasted Pineapple and RUM Mint Julep. Did you know that Juleps don’t have to be made with bourbon? They are simply a family of drinks that combine mint, sugar and crushed ice with pretty much whichever spirit you choose. As time has passed, however, bourbon has become synonymous with Mint Juleps which is not surprising considering that it is a drink that was made popular in the South and most specifically in Kentucky, the land of bourbon and horse racing.

I’ve made my share of  bourbon laced Mint Juleps but I also have friends that are not that fond of them; made right they are VERY bourbon forward so I went a different direction and we sure loved this Roasted Pineapple and Rum Mint Julep.

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Roasted Pineapple and Rum Mint Julep in a Mint Julep Cup

Though widely associated with the Kentucky Derby, the Julep is an international cocktail that was introduced to London by one Captain Marryatt who had discovered it on his trips to the South and brought this classic cocktail back to England with him. Thus started the journey of the Julep becoming an international favorite. I think they are so good that I often wonder why they are only popular for one day and one two minute horse race; let’s change that and we can start with this cocktail today!

Pineapple Rum Mint Julep

I was asked to create a cocktail using Cruzan® Pineapple Rum and since I had already made this Kentucky Oaks Lily Cocktail honoring the Kentucky Oaks race; I thought today I would combine my love of the Kentucky Derby with my love of Pineapple in a cocktail that carries some elements of both the race and a day that celebrates moms…you know…ME!

My favorite cake of all time is a Pineapple Upside Down cake so I’ve included some elements of that cake and roasted the pineapple in brown sugar which I’ve combined with rum, mint and a brown sugar simple syrup. I’m somewhat amazed that this cocktail came to be; I could have snacked on those finished pineapple tidbits all day long.

While I am not typically a big proponent of flavored liquors, I have always been a fan of Cruzan Rums. They’re subtle and made with good ingredients instead of artificial flavoring and I’ve had some excellent samples come my way; their Pineapple Rum is worthy of praise.

It could not be more perfect in this cocktail but I’ve already got plans for trying both a pineapple mojito and a pineapple margarita. You know what? I need to post more than one cocktail a week…I have SO many ideas and not enough days!

Roasted Pineapple and Rum Mint Juleps in Julep Cups

For those of you who might want to stick with something more traditional? I’ve made several Mint Juleps that are fantastic including this Sparkling Blackberry Mint Julep, a Muscavado and Vanilla Bean Mint Julep, and a Honey Peach Mint Julep. All with bourbon baby!

Whatever your pleasure this weekend, whether it be horses, margaritas or mom…try one of these Roasted Pineapple and Rum Mint Juleps; they are a great all summer long sipper…Cheers!

PIN IT! ‘Roasted Pineapple and Rum Mint Juleps’

Rum Served the standard silver mint julep cup with mint and pineapple garnish.
Pineapple Rum Mint Julep

Roasted Pineapple and Rum Mint Julep

A delicious cocktail that marries the flavors of a Pineapple Upside Down Cake with a Mint Julep.
5 average from less than 50 votes
Prep Time 15 minutes
Cook Time 30 minutes
Total Time 45 minutes
Course Cocktails, Friday Cocktails, Fruits
Cuisine American
Servings 2 cocktails
Calories 575 kcal


For the Brown Sugar Simple Syrup

  • 1 cup brown sugar
  • ½ cup water
  • 1 cup ice cubes

For the Roasted Pineapple

  • 1 cup fresh pineapple chunks fresh or canned
  • 2 tablespoons brown sugar

For the Pineapple Mint Julep

  • 8-10 pieces pineapple roasted
  • 2 ounces brown sugar simple syrup
  • 6-8 mint leaves
  • 2 ounces Pineapple Rum see notes
  • Crushed ice I put ice into a large Ziploc bag, covered it with a dish towel and banged it with the smooth side of a meat mallet


  • Chill your cocktail glasses.

To make Brown Sugar Simple Syrup

  • Combine sugar and water in a pot on medium heat.
  • Heat mixture until it simmers, stirring constantly. Once the sugar is dissolved, pour the mixture into a heat proof container and add the ice; stir until it melts and mixture is cool.
  • Pour cooled syrup into a bottle or jar and refrigerate until ready for use. Will keep for a couple of weeks in the fridge.

To Make the Pineapple and Rum Mint Juleps

  • Combine the pineapple chunks and brown sugar and mix to cover the pineapple. Lay the fruit on a baking sheet covered with foil and roast in a 400 degree oven until it starts to brown; about 20-30 minutes, turning over once midway. Watch carefully; it can go from brown to burned quickly. Cool.
  • In a large cocktail shaker, combine roasted pineapple chunks, brown sugar simple syrup and mint leaves.
  • Using a muddler or large spoon mash everything together. Add the rum, cover and shake vigorously for a few seconds.
  • Fill your chilled glasses with crushed ice above the rim
  • Strain the liquid from your shaker into the glass on top of the ice.
  • Garnish with a slice of pineapple and mint leaves. Serve immediately.


No Pineapple Rum to be found? No worries; just add another piece of two of the roasted pineapple tidbits to your shaker.


Nutrition Facts
Roasted Pineapple and Rum Mint Julep
Serving Size
1 Cocktail
Amount per Serving
% Daily Value*
* Percent Daily Values are based on a 2000 calorie diet.
Keyword Kentucky Derby, mint, mint julep, pineapple
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This is a sponsored conversation about Cruzan Pineapple Rum however all commentary is my own.

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  1. Nice change on the traditional Mint Julep! I’ve never made a rum one — definitely will have to. A demerera rum might be fun to use, too. Anyway, this is perfect for this weekend — thanks!

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