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Smoky Cinnamon Pineapple Old Fashioned Recipe

Smoky Cinnamon Pineapple Old Fashioned Recipe


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4.9 from 37 reviews

  • Total Time: 15 minutes
  • Yield: 2 1x

Description

Smoky charred cinnamon pineapple old fashioned cocktail blends tropical warmth with classic bourbon elegance. Caramelized pineapple and spiced cinnamon notes create a sophisticated sipping experience you won’t forget.


Ingredients

Scale
  • 2 oz (60 mL) bourbon
  • ½ cup (120 mL) fresh pineapple chunks
  • ¼ cup (60 mL) honey or brown sugar
  • ¼ cup (60 mL) water
  • ½ oz (15 mL) charred cinnamon pineapple syrup
  • 2 dashes Angostura bitters
  • 1 large ice cube
  • 1 cinnamon stick
  • 1 grilled pineapple wedge (for garnish)
  • 1 cinnamon stick (for garnish)
  • orange peel twist (optional, for garnish)

Instructions

  1. Grill Preparation: Heat a grill pan or outdoor grill to medium-high, creating the perfect environment for caramelizing pineapple chunks with intense, golden-brown char marks.
  2. Pineapple Charring: Arrange pineapple pieces on the hot surface, allowing each side to develop a deep, smoky caramelization that intensifies the fruit’s natural sweetness.
  3. Flavor Infusion: Transfer the charred pineapple to a saucepan, introducing a whole cinnamon stick, honey, and water to create a rich, aromatic liquid base.
  4. Syrup Development: Simmer the mixture on low heat, coaxing out deep, complex flavors and allowing the ingredients to meld into a harmonious, fragrant syrup.
  5. Steeping and Straining: Remove from heat, let the infusion rest to maximize flavor intensity, then strain carefully, extracting the pure, caramelized pineapple essence while discarding the cinnamon stick.
  6. Cooling Process: Allow the syrup to cool completely to room temperature, ensuring the concentrated flavors are ready to elevate the cocktail’s profile.

Notes

  • Grill with Precision: Watch pineapple chunks closely to achieve perfect caramelization without burning, turning pieces every 1-2 minutes for even charring.
  • Control Heat Levels: Maintain medium-high temperature to create deep golden-brown marks without scorching the fruit’s delicate sugars.
  • Infusion Timing: Allow full 10-minute steeping period for maximum flavor development, enabling cinnamon and pineapple to release complex aromatics.
  • Strain Carefully: Use fine-mesh strainer to capture maximum syrup essence while removing any potential burnt particles or cinnamon remnants.
  • Prep Time: 5 minutes
  • Cook Time: 10 minutes
  • Category: Drinks, Cocktails
  • Method: Grilling
  • Cuisine: American

Nutrition

  • Serving Size: 2
  • Calories: 200
  • Sugar: 24 g
  • Sodium: 1 mg
  • Fat: 0 g
  • Saturated Fat: 0 g
  • Unsaturated Fat: 0 g
  • Trans Fat: 0 g
  • Carbohydrates: 49 g
  • Fiber: 1 g
  • Protein: 1 g
  • Cholesterol: 0 mg