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Pineapple simple syrup brings a subtle, sweet tropical flavor to smoky bourbon in this Pineapple Old Fashioned.

A glass of pineapple old fashioned garnished with a pineapple wedge.

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Ingredients
How to Make a Pineapple Old Fashioned
Make Homemade Pineapple Simple Syrup
Glassware for an Old Fashioned Cocktail
More Bourbon and Whiskey Cocktail Recipes
Print the Recipe Card
Pineapple Old Fashioned Cocktail Recipe

Upgrade your next happy hour with this spin on a classic old fashioned. A tropical twist on a traditional old fashioned, this variation is a delicious next step for those who love the classic cocktail. The sweet pineapple flavor is subtle, only being brought in with the syrup, so the bourbon is still the star ingredient.

Like many cocktail enthusiasts, I'm a huge fan of cocktail variations. However, if I'm going to call a drink recipe an "old fashioned," I want to make sure it doesn't vary too far from its original recipe. So we're skipping pineapple rum, pineapple juice, lime juice, or brown sugar syrup in order to maintain the strong, smoky flavor of the bourbon.

Ingredients

Bourbon - Choose your favorite bourbon for this cocktail. I love Four Roses Single Barrel bourbon in my old fashioned cocktails.
Pineapple Syrup - Quick to make from the rind of fresh pineapple, pineapple simple syrup is the key ingredient in this cocktail.
Aromatic Bitters - These bitters add a warm spice element to this drink. Angostura bitters are the gold standard in aromatic bitters, but there are lots of other brands on the market. Choose your favorite. Substitute orange bitters or tropical bitters for the aromatic bitters, if that's what you have on hand.
Fresh pineapple (garnish) - Slices of fresh pineapple or flowery pieces of dried pineapple make a great garnish for this pineapple old fashioned.

How to Make a Pineapple Old Fashioned

Bourbon being poured into a mixing glass with ice.

In a mixing glass half filled with ice, combine bourbon, pineapple syrup and aromatic bitters.

A hand stirring a mixing glass filled with cocktail.

Stir for 10 seconds until well chilled.

Tip: Water is an ingredient in this cocktail, and we're adding it with the ice. Don't skip stirring with ice or only stir for 1-2 seconds. The ice needs time to melt slightly, contributing cold water to your drink.

A hand straining a pineapple old fashioned into a rocks glass.

Strain into a rocks glass filled with ice or one large ice cube. (Learn about clear ice in cocktails.)

A hand garnishing a drink with a piece of fresh pineapple.

Garnish with a slice of fresh pineapple. Sip and enjoy!

Make Homemade Pineapple Simple Syrup

Pineapple syrup is easy to make at home with just three ingredients, one being fresh pineapple rinds! Get the recipe, tips, and directions over on my homemade pineapple syrup page.

Glassware for an Old Fashioned Cocktail

Old Fashioned cocktails are traditionally served in rocks glasses - flat bottomed glasses with straight sides. It can sometimes be called an old fashioned glass.

If you don't have specialty glassware on hand, try using a juice glass. While not as heavy as a traditional rocks glass, the juice glasses in most household cupboards hold 8 to 9 ounces, which is the size you're looking for.

More Bourbon and Whiskey Cocktail Recipes

Looking for more delicious ways to sip bourbon and whiskey? Try my popular coffee old fashioned, a frothy bourbon ginger sour, or a fizzy ginger bourbon cocktail.

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