Smoky-Sweet Charred Cinnamon Pineapple Old Fashioned Recipe

My mixology adventure recently discovered a charred cinnamon pineapple old fashioned that changed cocktail expectations forever.

Caramelized edges of sweet tropical fruit dance with smoky whiskey notes in unexpected harmony.

Bartenders worldwide seek unique flavor combinations, but this recipe stands apart with its bold complexity.

Flames and spice merge into liquid magic, creating depth beyond standard cocktail formulas.

Sophisticated yet approachable, each sip tells a story of culinary creativity and expert technique.

Sharp cinnamon undertones complement the pineapple’s natural sweetness, making every glass an invitation to sensory exploration.

You’ll want to master this technique and impress everyone at your next gathering.

Why This Old Fashioned Is Full of Warm Flavor

• Grilling pineapple elevates its natural sweetness, creating a smoky-caramelized taste that takes a classic cocktail to extraordinary levels.
• This recipe requires minimal cooking skills, with simple steps that deliver a sophisticated drink perfect for impressing guests without complex techniques.
• An elegant cocktail that's ideal for dinner parties, summer gatherings, or relaxed weekend evenings, offering a unique twist on a traditional Old Fashioned.
• The homemade cinnamon-pineapple syrup can be stored and used in multiple drinks or desserts, extending the recipe's versatility beyond a single cocktail.

Ingredients for Charred Cinnamon Pineapple Old Fashioned

• Bourbon, Rye Whiskey: Rich, warming base spirit with deep caramel and oak notes, choose a high-quality whiskey for best flavor profile.
• Pineapple: Fresh, sweet tropical fruit that will be grilled for deep caramelized flavor and smoky complexity.

• Honey, Brown Sugar: Natural sweeteners that add depth and richness to the pineapple syrup, honey offers floral notes while brown sugar provides deeper molasses undertones.
• Cinnamon Stick: Warm, aromatic spice that infuses the syrup with a gentle, woody sweetness and complex flavor.
• Water: Helps dissolve sweeteners and create smooth, balanced syrup consistency.

• Ice: Provides chilling and dilution, large cube or sphere preferred for slower melting and minimal water interference.
• Optional Garnish: Fresh pineapple chunk or cinnamon stick can enhance visual appeal and aromatic experience of the cocktail.

How to Mix and Char the Perfect Cocktail

Step 1: Fire Up The Grill Pan

Heat a grill pan over medium-high flame until it’s sizzling hot. Toss fresh pineapple chunks onto the surface and cook until golden brown marks appear, about 2-3 minutes per side. The goal is beautiful caramelization with slight char edges.

Step 2: Craft Flavor-Packed Syrup

• Grilled pineapple chunks
• Whole cinnamon stick
• Honey
• Water

Combine all ingredients in a small saucepan. Bring mixture to a gentle simmer, letting flavors meld together. Cook for 5 minutes, then remove from heat. Allow syrup to rest and steep for additional 10 minutes, allowing cinnamon to infuse deeply.

Step 3: Strain And Prepare Liquid Gold

Carefully remove cinnamon stick from syrup. Strain pineapple chunks, pressing gently to extract maximum flavor. Let syrup cool completely to room temperature.

Step 4: Mix Cocktail Magic

In a cocktail shaker, combine bourbon, cooled pineapple-cinnamon syrup, and bitters. Add ice and shake vigorously until thoroughly chilled.

Step 5: Serve With Flair

Strain cocktail into a rocks glass filled with fresh ice. Garnish with a grilled pineapple wedge and cinnamon stick. Enjoy your sophisticated, smoky-sweet libation.

Cocktail Tips for Flavor and Presentation

• Char with Care: Watch the pineapple closely while grilling to prevent burning, ensuring perfect caramelization without bitter scorching.
• Steep Smartly: Let the cinnamon stick infuse fully in the syrup to maximize flavor depth, creating a rich aromatic base for your cocktail.
• Swap Sugar Sources: Replace honey with brown sugar or maple syrup for different flavor profiles and dietary preferences.
• Chill Before Mixing: Cool the pineapple syrup completely before adding to the cocktail to maintain optimal drink temperature and prevent dilution.
• Enhance Presentation: Garnish with a fresh grilled pineapple wedge or cinnamon stick to elevate the visual appeal and add an extra layer of flavor complexity.

Best Way to Keep Leftovers (If There Are Any!)

• Transfer cooled pineapple cinnamon syrup into an airtight glass container and store in the refrigerator for up to 1 week, preserving its rich, sweet flavor.
• Place leftover grilled pineapple pieces in a freezer-safe bag, seal tightly, and freeze for future cocktails or dessert toppings, lasting up to 3 months.
• When ready to reuse, slowly reheat the syrup in a small saucepan over low heat, stirring occasionally to maintain its original consistency and prevent burning.
• Mix leftover syrup into yogurt, drizzle over pancakes, or use as a glaze for grilled meats for versatile culinary enjoyment.

Foods That Go Well with This Drink

• Select charred meat or vegetable skewers that echo the cocktail's smoky, caramelized notes, creating a harmonious flavor profile.
• Choose warm cinnamon-based treats like apple crisp or bread pudding that mirror the cocktail's sweet and spicy undertones.
• Serve a selection of aged gouda, sharp cheddar, or manchego to balance the drink's richness and highlight its complex flavors.
• Create a board featuring prosciutto, dried pineapple, macadamia nuts, and candied ginger to amplify the cocktail's tropical and sweet elements.

Twists to Try with This Cocktail

• Tropical Rum Variation: Replace bourbon with white rum for a Caribbean-inspired cocktail with enhanced tropical flavors.
• Spiced Agave Twist: Swap honey for agave nectar and add a pinch of cayenne pepper for a spicier, more complex drink.
• Mocktail Option: Remove alcohol completely and use pineapple juice with sparkling water for a family-friendly version.
• Diabetic-Friendly Adaptation: Use sugar-free sweetener instead of honey, and choose a zero-carb bourbon or rum alternative to reduce sugar content.

Cocktail FAQ Section

• What type of bourbon works best for this cocktail?

Choose a high-quality bourbon with caramel or vanilla notes like Woodford Reserve or Buffalo Trace, which complement the grilled pineapple and cinnamon flavors perfectly.

• Can I make the pineapple syrup ahead of time?

Yes, you can prepare the pineapple cinnamon syrup up to 5 days in advance and store it in the refrigerator in a sealed container for easy cocktail preparation.

• Do I need any special equipment to make this cocktail?

You’ll need a grill pan or outdoor grill, a saucepan for making syrup, and a cocktail strainer. A muddler can help enhance the pineapple flavor if you want to muddle some fresh pineapple pieces.

• Is this cocktail sweet or strong?

This cocktail balances sweetness from the grilled pineapple and honey with the strong bourbon base, creating a complex and smooth drinking experience with moderate sweetness.

Charred Cinnamon Pineapple Old Fashioned Recipe

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4.5 from 9 reviews

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

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Description

Smoky “charred cinnamon pineapple old fashioned” cocktails blend tropical sweetness with bourbon’s rich depth. Spirited mixologists craft this elevated classic, delivering complex layers of caramelized fruit and warming spice that dance beautifully in each sip.

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Ingredients

Scale 1x2x3x

Fruits and Base:

• ½ cup (120 milliliters) fresh pineapple chunks
• 2 ounces (60 milliliters) bourbon
• 1 large ice cube
• 1 grilled pineapple wedge (for garnish)

Sweeteners and Syrups:

• ¼ cup (60 milliliters) honey or brown sugar
• ¼ cup (60 milliliters) water
• ½ ounce (15 milliliters) charred cinnamon pineapple syrup

Spices and Aromatics:

• 1 cinnamon stick
• 1 cinnamon stick (for garnish)
• 2 dashes Angostura bitters
• Orange peel twist (optional, for garnish)

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Instructions

1. Prepare a grill pan or outdoor grill, heating to medium-high temperature for optimal caramelization of pineapple chunks.
2. Carefully place pineapple pieces onto the heated surface, allowing each side to develop deep golden-brown char marks for 2-3 minutes.
3. Transfer charred pineapple to a small saucepan, combining with a whole cinnamon stick, honey, and water.
4. Reduce heat and gently simmer the mixture, allowing flavors to meld and intensify for approximately 5 minutes.
5. Remove the saucepan from heat, letting the infusion steep and develop complex aromatics for an additional 10 minutes.
6. Extract the cinnamon stick from the liquid and carefully strain the syrup, capturing the rich, caramelized pineapple essence.
7. Allow the strained syrup to cool completely, ensuring it reaches room temperature before using in the cocktail preparation.

Notes

• Char pineapple slowly to develop deep caramelized flavors without burning, which enhances the cocktail’s complexity.
• Experiment with alternative sweeteners like agave or maple syrup for different flavor profiles and dietary preferences.
• Use fresh, ripe pineapple for maximum natural sweetness and optimal grilling results, avoiding underripe or overripe fruit.
• Consider making extra pineapple-cinnamon syrup to use in other cocktails or as a dessert topping for added versatility.

• Prep Time: 5 minutes
• Cook Time: 10 minutes
• Category: Drinks, Cocktails
• Method: Grilling
• Cuisine: American

Nutrition

• Serving Size: 1
• Calories: 300
• Sugar: 34 g
• Sodium: 5 mg
• Fat: 0 g
• Saturated Fat: 0 g
• Unsaturated Fat: 0 g
• Trans Fat: 0 g
• Carbohydrates: 76 g
• Fiber: 1 g
• Protein: 1 g
• Cholesterol: 0 mg