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Freeman's First Date

Freeman's First Date is a cocktail that will take you back to the 90s, when you roamed the mall, Orange Julius in hand. This Old Fashioned riff features Orange Tiger, Plantation Pineapple Rum, and Zaya Rum, blended together with a touch of Solerno Blood Orange Liqueur and vanilla syrup, for a creamy and citrusy cocktail that will transport you back to your mall days.

Quick note: While we usually recommend that you just use your favorite spirits in these cocktails, the pineapple in Plantation Pineapple and the strong vanilla notes in the Zaya are pretty essential for this cocktail.

Difficulty Level


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  • 1 oz Orange Tiger Bourbon Barrel-Aged Orange Liqueur
  • 3/4 oz Plantation Pineapple Rum
  • 1/2 oz Zaya Rum
  • 1/2 oz Solerno Blood Orange Liqueur
  • 1/2 oz vanilla syrup (recipe below)
  • 1/4 oz rye whiskey
  • 2 dashes Angostura bitters
  • 2 dashes orange bitters

Vanilla Syrup

  • 1 cup water
  • 1 cup granulated sugar
  • 1 vanilla bean, split lengthwise

Mix it up


  1. To make the vanilla syrup, combine water and sugar in a small saucepan and heat over medium heat, stirring occasionally, until the sugar is dissolved.
  2. Add the split vanilla bean and continue to heat for 10-15 minutes, stirring occasionally, until the mixture has thickened and become syrupy.
  3. Remove the pan from the heat and let the syrup cool.
  4. Once cooled, remove the vanilla bean and transfer the syrup to a clean jar or bottle for storage.
  5. In a mixing glass or shaker, combine Orange Tiger Bourbon Barrel-Aged Orange Liqueur, Plantation Pineapple Rum, Zaya Rum, Solerno Blood Orange Liqueur, vanilla syrup, rye whiskey, and both Angostura and orange bitters.
  6. Add ice and stir or shake for about 10-15 seconds, until the ingredients are well combined and chilled.
  7. Strain the mixture into a rocks glass filled with ice.
  8. Garnish with a slice of blood orange or orange peel.
  9. Enjoy!

About the author

About Toledo Spirits Co.

Welcome to Toledo Spirits, where tradition meets innovation in every glass. We are storytellers in the art of cocktails. Our passion lies in crafting spirits that inspire and reimagine classic cocktails with a modern twist. At Toledo Spirits, we believe that the essence of a great cocktail goes beyond its ingredients. It's about the experience, history, and balance each taste offers.

Our craft spirits are the foundation of this philosophy, each meticulously distilled to ensure the highest quality and unique character.