The Charred Cinnamon Pineapple Old Fashioned is a smoky, sweet, and spicy twist on the classic Old Fashioned cocktail. With caramelized pineapple, warm cinnamon, and rich bourbon, this cocktail delivers a perfect balance of deep flavors and smooth sipping. Ideal for whiskey lovers looking for a creative and flavorful drink, it’s perfect for cozy nights or special occasions.
Why You’ll Love This Recipe
- Smoky & Sweet – The charred pineapple adds a deep caramelized sweetness.
- Classic with a Twist – A fresh take on the beloved Old Fashioned.
- Warm & Inviting – Cinnamon complements the whiskey beautifully.
- Impressive Yet Easy – Simple ingredients with a bold flavor.
- Perfect for Any Occasion – Great for sipping on a cool evening or serving at gatherings.
Ingredients
(Tip: You’ll find the full list of ingredients and measurements in the recipe card below.)
- 2 oz bourbon (or rye whiskey)
- 1 slice fresh pineapple
- 1 cinnamon stick
- ½ oz simple syrup (or honey syrup)
- 2 dashes Angostura bitters
- Ice (large cube preferred)
- Orange peel (for garnish)
Directions
- Char the Pineapple – Heat a grill or cast-iron pan over high heat. Sear the pineapple slice until caramelized and slightly blackened, about 1-2 minutes per side. Let cool slightly.
- Muddle – In a mixing glass, muddle the charred pineapple with the simple syrup and bitters.
- Add Bourbon & Stir – Pour in the bourbon and add a large ice cube. Stir well for 30 seconds.
- Flame the Cinnamon Stick – Light a cinnamon stick for a few seconds, blow it out, and place it in the glass for a smoky aroma.
- Garnish & Serve – Express an orange peel over the drink and drop it in. Optionally, place a small pineapple wedge on the rim. Enjoy!
Servings and Timing
- Servings: 1 cocktail
- Prep Time: 5 minutes
- Total Time: 5 minutes
Variations
- Spicy Version: Add a pinch of cayenne or muddle a jalapeño slice.
- Smokier Flavor: Use a smoked glass or add a splash of mezcal.
- Sweeter Touch: Replace simple syrup with maple syrup or honey.
- Fruity Twist: Muddle in a cherry for extra depth.
- Non-Alcoholic: Use non-alcoholic whiskey or a mix of apple cider and bitters.
Storage/Reheating
- Make-Ahead: The charred pineapple can be prepped in advance and stored in the fridge for 2 days.
- Leftover Syrup: Extra simple syrup lasts up to a month refrigerated.
FAQs
Can I use canned pineapple?
Fresh is best for charring, but canned pineapple (drained) works in a pinch.
What’s the best bourbon for this cocktail?
A smooth bourbon like Woodford Reserve, Buffalo Trace, or Four Roses works well.
Can I use a different type of whiskey?
Yes! Rye whiskey adds a spicier kick, while Scotch gives a smoky depth.
How do I get the best char on the pineapple?
Use a hot grill or pan and let the pineapple caramelize without moving it.
Can I skip the cinnamon stick?
Yes, but it adds warmth and aroma that enhances the drink.
What’s a good pairing for this cocktail?
Serve with spiced nuts, dark chocolate, or grilled meats for a complementary experience.
How do I make the simple syrup at home?
Dissolve equal parts sugar and water over low heat until fully mixed.
Can I batch-make this for a party?
Yes! Pre-muddle the pineapple with syrup and bitters, then mix individual servings.
Should I use crushed ice or a large cube?
A large cube melts slower, keeping the drink from getting diluted too quickly.
Can I make this drink without muddling?
Yes, infuse the bourbon with charred pineapple for a smoother texture.
Conclusion
The Charred Cinnamon Pineapple Old Fashioned is a bold, smoky, and slightly sweet twist on a timeless cocktail. Whether you’re sipping it by the fire or serving it at a gathering, this drink delivers a unique flavor experience that whiskey lovers will appreciate. Try it today and elevate your cocktail game!
Print
Charred Cinnamon Pineapple Old Fashioned
- Prep Time: 5 minutes
- Cook Time: 10 minutes
- Total Time: 15 minutes
- Yield: 1 cocktail 1x
- Category: Cocktails, Drinks
- Method: Stirred
- Cuisine: American, Craft Cocktails
Description
This Charred Cinnamon Pineapple Old Fashioned is a smoky, sweet, and spiced twist on the classic cocktail. Featuring grilled pineapple, warm cinnamon, bourbon, and bitters, this drink delivers rich, caramelized flavors that make it perfect for sipping year-round.
Ingredients
For the Charred Pineapple & Cinnamon Syrup:
- 1/2 cup fresh pineapple chunks
- 1 cinnamon stick
- 1/4 cup honey or brown sugar
- 1/4 cup water
For the Cocktail:
- 2 oz bourbon
- 1/2 oz charred cinnamon pineapple syrup (from above)
- 2 dashes Angostura bitters
- 1 large ice cube
- 1 grilled pineapple wedge (for garnish)
- 1 cinnamon stick (for garnish)
- Orange peel twist (optional, for garnish)
Instructions
Step 1: Make the Charred Cinnamon Pineapple Syrup
- Grill the Pineapple: Heat a grill pan or outdoor grill over medium-high heat. Add pineapple chunks and grill for 2-3 minutes per side, until caramelized.
- Make the Syrup: In a small saucepan, combine grilled pineapple, cinnamon stick, honey (or brown sugar), and water. Simmer for 5 minutes, then remove from heat and let steep for 10 minutes.
- Strain & Cool: Remove the cinnamon stick, strain out the pineapple, and let the syrup cool.
Step 2: Mix the Cocktail
- In a mixing glass, combine bourbon, charred pineapple syrup, and bitters.
- Add ice and stir for 30 seconds until well chilled.
- Strain into a rocks glass over a large ice cube.
Step 3: Garnish & Serve
- Garnish with a grilled pineapple wedge, cinnamon stick, and an optional orange peel twist.
- Enjoy this smoky, spiced, and slightly tropical take on an Old Fashioned!
Notes
- Whiskey Variations: Try rye whiskey for a spicier kick or dark rum for extra tropical vibes.
- Make it Smokier: Use a smoked cinnamon stick or a smoking gun to infuse extra depth.
- Batch Option: Multiply ingredients and mix in a pitcher for serving at parties!