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Vanilla Bean Old Fashioned with Brown Sugar Glazed Pineapple

Pineapple Old Fashioned with Vanilla Bean Syrup

I promised a pineapple inspired drink for Father's Day, so here you go! I took the flavors of pineapple upside down cake and used them to make Sushil a Pineapple Old Fashioned with Vanilla Bean Syrup! What is more classic than that? 

It's not uncommon to see vanilla in an old fashioned recipe, or cherries as a garnish so using a brown sugar glazed pineapple just simply kicks it up a notch. The pineapple doesn't over power this classic cocktail, but is a definitely a pretty garnish and something sweet for your honey ;) 


  • 2 oz. bourbon

  • 2 tsp vanilla bean syrup, or to taste

  • 2-3 splashes of angustora bitters

  • brown sugar glazed pineapple and good brandied or bourbon cherries for garnish

Vanilla Bean Simple Syrup

  • 1/2 cup brown sugar

  • 1/2 Madagascar vanilla bean

  • 1/3 cup water

  • 1 tsp vanilla extract

Vanilla Bean Old Fashioned

To make the vanilla bean simple syrup start by heating the brown sugar and water in a small pot. Cut the vanilla bean in half with a sharp knife, then scrape the inside of the vanilla bean to remove the tiny seeds. Add seeds and pod to the pot with sugar and water. Let everything come to a simmer, and cook for 1-2 minutes. Then remove from heat and let cool. After mixture cools add vanilla extract. 

To make the brown sugar glazed pineapple mix together 3 tablespoons of brown sugar and 1 teaspoon of chili powder (optional) in a shallow dish. Place thin slices of fresh or canned pineapple n sugar and chili mix. Cover both sides of pineapple then grill or broil until the outsides of the pineapple is caramelized.

For the old fashioned place bourbon, vanilla bean syrup, and bitters in a cocktail glass. Add one large cube of ice. Stir, and garnish with pineapple and cherries. 


  1. Store unused simple syrup in the fridge for 7-10 days. Use to sweeten coffee, tea, or over pancakes!