Grilled Pineapple Old Fashioned

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I’ve had the fun pleasure of hosting my sister-in-law Erin and her good friend Brittany during their visit to Miami this week. And as with any friends or family visiting, in addition to me making sure I have a few new meals to test out on them, a new signature cocktail is always in the works.

With Grilling Week on the blog a day away from coming to a close, I thought it only fitting to greet my guests with a beverage that embodied this week’s theme.

Today, I share with you my Grilled Pineapple Old Fashioned. With only two ingredients, it is easier to make than the traditional. It utilizes the warmth of the grilled fruit to create its own “simple syrup” from the ice it melts in the shaker. Shaken gently with your choice of bourbon and strained over ice, this cocktail delivers on flavor and punch. And as with all drinks involving fresh fruit, it’s healthy! 🙂

To will the warmer months into being, check out this recipe and whip a batch of these up next time you’re mixing drinks. You’ll forget all about the cold the moment the flavorful bourbon touches your lips.

Grilled Pineapple Old Fashioned

(recipe serving size – 1 cocktail)

For the cocktail:

4 oz bourbon (Bulleit was my weapon of choice)

1 slice of fresh pineapple, 1/2 inch thick

A few dashes of orange bitters

Using an indoor grill pan or an outdoor grill, grill the pineapple for 3 minutes on each side over medium to medium-high heat. Add the slice of pineapple to a shaker filled with 1 cup of ice. Muddle for 20-30 seconds, leaving only a few cubes of ice still frozen.

Add the bourbon to the shaker and shake for a few seconds, just enough to incorporate the pineapple and the alcohol.

Pour the contents of the shaker into a tumbler filled with ice through a strainer, making sure none of the pineapple chunks fall into the glass. Stir in the orange bitters and enjoy while cold!

Tip: While using an outdoor grill with charcoal and/or wood will add another layer of depth and smokiness to the drink, just make sure to clean the rack your pineapple will be resting on well before grilling the fruit. The last thing you want is remnants of the burgers you grilled floating around in your glass.

5 thoughts

  1. Mmm… This sounds great. I’ll have to find a pineapple and check it out; maybe some smoky flavor would be a good touch, like you said. Sort of like a mezcal, but pineapple! Does the fruit give enough sweetness to the drink?


    1. Hey! I’m so glad you like the recipe. I personally think the drink is plenty sweet. Using bourbon instead of rye whiskey adds additional sweetness as well, making up for the lack of simple syrup.


    1. Thanks for the shoutout and the review. I love your assessment and you are spot on with needing sweet pineapple and enough grilling time. You want really decent grill marks on the pineapple before muddling it. And don’t be afraid to up the amount of pineapple if you don’t feel the fruit is sweet enough. I personally don’t like sweet drinks, which is what drew me to make this cocktail this particular way. With that said, I’m excited to try adding a few of the more traditional Old Fashioned ingredients to see where it takes the beverage. Cheers!


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