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rye whiskey, social hour, tom macy, cocktail, classic cocktail

Pineapple Julep



  • 2¼ oz bourbon

  • ¾ oz pineapple syrup 

  • 10-12 mint leaves - no stems


In a julep cup or rocks glass, muddle the mint leaves with the simple syrup - be careful not to "over-muddle". Add the whiskey and fill 3/4 of the way with crushed ice, or the smallest ice cubes you have. 


Gently stir until frost appears on the outside of the glass.  If you have the time (and patience), let it sit for a minute or so for optimal chill and dilution.  Top with more crushed ice so it form a mound above the cup/glass. Garnish with mint sprigs and peach slices. 

If you make a Pineapple Julep, let me see!  

Tag a photo with #socialhourcocktails on Instagram.


You'll find a recipes for a Pineapple Julep in several old cocktail books, but they'll look nothing like what you would imagine.   There's gin, raspberry, maraschino, sparkling wine (William Schmidt's recipe in his legendary 1891 "The Flowing Bowl" includes ice cream), with pineapple only playing a cursory role.


While I'm sure these are delightful drinks, I've never been able to shake my initial presumption of what a pineapple julep was when I first heard the name: a Mint Julep, plus pineapple.  So that is what this recipe is for here, history be damned (with all due respect, of course). The pineapple syrup requires some extra prep, but the payoff is worth it.


For more details on julep preparation, history

and those cool silver cups, visit the Mint Julep page.

Pineapple Syrup

  • 2 cups of fresh pineapple cubes

  • 2 cups sugar 


  1. In a mixing bowl stir the sugar and pineapple together so the cubes are entirely coated.  Cover and let sit for at least 3 hours, but the longer the better.  When finished sugar should be all or mostly dissolved and the mixture should be soupy.    

  2. Blend with an immersion blender  - or transfer and blend in a blender/food processor - until smooth.  

  3. Strain with a mesh strainer, ideally one that’s not too  fine.  This last step is fairly tedious because the mixture will be very thick.  You’ll need to frequently scrape the bottom of the strainer with a spoon to keep it flowing.  Keep at it!


Note: 1 whole pineapple usually gets you around 4 cups, or 1 quart, of cubes.  If you don’t need that much you can opt for those pre-cut containers of pineapple you find at many supermarkets.   

Pineapple Syrup
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