Sizzling Smoky Cinnamon Pineapple Old Fashioned Recipe
As the sun dips below the horizon, a smoky cinnamon pineapple old fashioned cocktail beckons with its sultry allure.
This unique twist on a classic whiskey drink blends rich, warming spices with tropical sweetness.
Bourbon meets caramelized pineapple in a mesmerizing dance of flavors that tantalizes the senses.
Cinnamon’s gentle heat weaves through the smoky undertones, creating a sophisticated sip that promises pure indulgence.
Each carefully crafted element elevates this cocktail from ordinary to extraordinary.
The result is a drink that whispers of adventure and sophistication.
Don’t miss the chance to impress your guests with this remarkable libation that redefines the art of cocktail making.
Quick Recipe Overview
Prep Time: 5 minutes
Cook Time: 10 minutes
Total Time: 15 minutes
Calories: 300 kcal
Servings: 1
Ingredients for Charred Cinnamon Pineapple Old Fashioned
For Grilling:
Pineapple: Fresh, ripe chunks create a caramelized base with sweet smoky undertones that elevate the cocktail's complexity.
For Sweetening and Flavor Infusion:
Honey, Brown Sugar: Natural sweeteners that add depth and balance to the pineapple syrup.
Cinnamon Stick: Warm, aromatic spice that infuses the syrup with rich, comforting notes.
Water: Helps dissolve sweeteners and extract maximum flavor during syrup preparation.
For Cocktail Base:
Bourbon or Whiskey: Robust spirit that provides a strong, classic foundation for the Old Fashioned.
Bitters: Concentrated botanical blend that adds complexity and traditional cocktail character.
Orange Peel: Bright citrus essence that complements the smoky-sweet pineapple and provides aromatic garnish.
Ice: Chills and dilutes the cocktail, ensuring a smooth and balanced drinking experience.
Tools for Mixing a Pineapple Old Fashioned Right
Grill Pan or Outdoor Grill: Essential for charring and caramelizing pineapple chunks evenly.
Small Saucepan: Perfect for creating the infused pineapple-cinnamon syrup.
Fine-Mesh Strainer: Helps remove pineapple chunks and cinnamon stick from the syrup.
Measuring Cups and Spoons: Ensures precise ingredient quantities for consistent flavor.
Cutting Board and Knife: Needed for preparing pineapple chunks before grilling.
Wooden Spoon: Great for stirring and managing syrup while cooking.
How to Craft a Charred Cinnamon Pineapple Cocktail
Prepare Pineapple Sear the pineapple chunks on a hot grill pan until golden brown edges develop, creating a caramelized exterior with smoky flavor notes.
Create Infused Syrup Combine grilled pineapple pieces with a fragrant cinnamon stick, sweet honey, and water in a small saucepan, allowing the mixture to simmer and develop rich, deep flavors.
Craft Liquid Base Strain the warm syrup, discarding pineapple chunks and cinnamon stick, then let the liquid cool to room temperature, concentrating its intense tropical essence.
Mix Cocktail Fill a rocks glass with ice, pour bourbon, add the cooled pineapple-cinnamon syrup, and stir gently to blend the complex flavors.
Finish and Garnish Twist an orange peel over the drink to release citrus oils, then drop it into the glass for an aromatic final touch that elevates the entire cocktail experience.
Mixologist Tips for the Perfect Sip
Grill Master Trick: Pat pineapple chunks dry before grilling to ensure perfect caramelization and prevent sticking. A paper towel works wonders for removing excess moisture.
Smoky Depth Boost: Use a cast-iron grill pan for deeper char marks and enhanced smoky flavor that elevates the cocktail's complexity.
Sugar-Free Option: Swap honey with sugar-free maple syrup or stevia for a low-carb, diabetic-friendly version of the cocktail that maintains rich flavor profiles.
Make-Ahead Magic: Prepare pineapple cinnamon syrup up to one week in advance and store in an airtight container in the refrigerator for convenient entertaining and instant cocktail preparation.
Spice Lovers' Twist: Add a pinch of cayenne pepper to the syrup for a subtle heat that beautifully complements the sweet pineapple and warm cinnamon notes.
Serve the Pineapple Old Fashioned with Flair
Tropical Cocktail Companion: Serve with grilled shrimp skewers or coconut rice for a complementary tropical flavor profile.
Dessert Pairing Perfection: Drizzle remaining pineapple syrup over vanilla ice cream or pound cake for a delightful post-cocktail sweet treat.
Garnish Galore: Top the drink with a charred pineapple wedge, sprinkle of cinnamon, or candied pineapple chunk to enhance visual and flavor appeal.
Brunch Brilliance: Create a brunch cocktail station where guests can customize their old fashioned with different grilled fruit syrups and garnishes.
Storing Your Cocktail Components Like a Pro
Flavor Preservation Tricks: Store leftover cinnamon pineapple syrup in an airtight glass container in the refrigerator for up to 7 days, ensuring maximum taste retention.
Batch Preparation Strategy: Create larger syrup quantities during weekend cooking sessions, storing extra batches in sealed mason jars for quick cocktail preparation throughout the week.
Ingredient Freshness Technique: Keep fresh pineapple chunks sealed in a container with a tight lid in the refrigerator for 2-3 days before grilling to maintain optimal texture and sweetness.
Cocktail Prep Shortcut: Prepare grilled pineapple and cinnamon syrup in advance, allowing busy hosts to quickly assemble drinks during spontaneous gatherings or unexpected guest arrivals.
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
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.
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.
Flavor Infusion: Transfer the charred pineapple to a saucepan, introducing a whole cinnamon stick, honey, and water to create a rich, aromatic liquid base.
Syrup Development: Simmer the mixture on low heat, coaxing out deep, complex flavors and allowing the ingredients to meld into a harmonious, fragrant syrup.
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.
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.
Focus: Focused on mastering culinary methods and food science, immersive externships, hands‑on training in industry‑standard kitchen labs, and equipping graduates for roles in restaurant operations.
William Hawkins isn’t just a chef, he’s a storyteller through food. From his hometown of Louisville, KY, he’s spent years refining his craft, turning local ingredients into something extraordinary.
With classical training from Sullivan University and a career marked by innovation, mentorship, and Southern soul, William approaches every recipe with purpose. His kitchen is where old techniques meet fresh ideas, and where comfort food gets a thoughtful, modern twist.
When he’s not building dishes from the ground up, he’s out gathering inspiration from nature, markets, and the stories people share around the table.
William Hawkins
Founder & Culinary Director
Expertise
Education
Sullivan University, Louisville, KY
William Hawkins isn’t just a chef, he’s a storyteller through food. From his hometown of Louisville, KY, he’s spent years refining his craft, turning local ingredients into something extraordinary.
With classical training from Sullivan University and a career marked by innovation, mentorship, and Southern soul, William approaches every recipe with purpose. His kitchen is where old techniques meet fresh ideas, and where comfort food gets a thoughtful, modern twist.
When he’s not building dishes from the ground up, he’s out gathering inspiration from nature, markets, and the stories people share around the table.