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This charred cinnamon pineapple old fashioned is my absolute favorite spin on a classic cocktail for special nights and fun gatherings. Sweet grilled pineapple and a hint of cinnamon bring out the bourbon’s warmth, while the charred flavor gives it a depth that always gets everyone talking. I discovered this beauty at a backyard barbecue and now it is a go-to choice whenever I want to treat friends or just relax on the porch with a drink that feels like a mini vacation.
When I first tried this version, I was amazed at how much the charred fruit turned a classic into something unforgettable. Now my friends request it for every summer party.
Ingredients
- Bourbon: two ounces pick a smooth rich style for backbone in your cocktail your favorite sipping bourbon is perfect
- Charred cinnamon pineapple syrup: half ounce this brings sweet depth and a cozy cinnamon warmth I make it by slowly simmering pineapple with sugar and cinnamon then charring for that smoky edge
- Angostura bitters: two dashes creates complexity and balance choose a fresh bottle for maximum aroma
- Charred cinnamon pineapple slice: one for garnish this adds an irresistible aroma and makes each glass look festive and inviting
- Aim for fresh ripe pineapple when you can: the natural sugars caramelize on the grill for the best syrup and garnish
Step-by-Step Instructions
- Char the Pineapple:
- Slice your fresh pineapple into thick half inch rounds and heat your grill or skillet to medium high. Lay the pieces on and cook three to four minutes per side until dark golden marks appear and the pineapple smells fragrant. For indoor prep use a skillet with a little oil and cook until caramelized on both sides. Let cool a bit before using.
- Make the Syrup:
- Simmer chopped pineapple with sugar cinnamon and a splash of water on low until soft and syrupy. Char the mixture again in a hot pan to infuse a smoky flavor. Strain and chill the syrup you will want to save some extra for more cocktails later.
- Mix Your Drink:
- Add bourbon charred cinnamon pineapple syrup and bitters to a mixing glass. Fill halfway with ice then stir gently for twenty to thirty seconds cooling and diluting just right so the flavors meld beautifully.
- Strain and Garnish:
- Fill a rocks glass with fresh ice. Strain the mixture over the ice then finish by adding a luscious slice of charred pineapple on top for garnish. The aroma alone will have you coming back for another sip.
- Enjoy:
- Now take a moment for yourself and savor the mix of smoky sweet and spiced flavors. Each sip will remind you of the sunny warmth of grilled pineapple and the comfort of cinnamon.
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Charred cinnamon pineapple is my stand out ingredient. The smell that fills my kitchen while grilling pineapple brings back memories of family barbecues where we laughed and shared stories late into the night. This cocktail is always tied to those easy joyful moments for me.
Storage Tips
Keep leftover charred pineapple syrup in an airtight container in the fridge where it will hold up well for about a week. Make your cocktails fresh for best results but you can mix bourbon and syrup ahead and chill overnight if needed. Always add ice and garnish just before serving.
Ingredient Substitutions
Try spiced rum in place of bourbon for a different flavor twist or switch Angostura for orange bitters if you want a brighter taste. Canned pineapple can stand in if fresh is out of season but fresh caramelizes best.
Serving Suggestions
Serve over a big chunk of ice with lots of charred pineapple for garnish. This cocktail is a great pairing with grilled shrimp tacos barbecue chicken or anything fresh from the grill.
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A Little History
The Old Fashioned dates back to the early eighteen hundreds and became a hit in American bars for its balance and simplicity. Bringing in charred fruit and cinnamon gives a familiar drink a tropical flair that feels both new and timeless.
Common Recipe Questions
- → What does charring pineapple add to the cocktail?
Charring pineapple caramelizes natural sugars, bringing out smoky depth and sweet complexity to balance the bourbon and cinnamon.
- → Can I make cinnamon pineapple syrup in advance?
Yes, prepare the syrup ahead and refrigerate it in an airtight container. It will keep for about one week, ready for your next cocktail.
- → How do I adjust the sweetness of the drink?
Modify the amount of syrup to meet your taste. For less sweetness, use less syrup or add a splash of citrus juice for balance.
- → What type of bourbon works best?
Choose a smooth, rich bourbon for the best flavor. Sweeter or spicier styles both pair well, so opt for what you enjoy most.
- → Is this cocktail suitable for entertaining?
Absolutely. Its striking garnish, unique flavor, and ease of preparation make it ideal for gatherings and special occasions.
- → Can I use a skillet instead of a grill for charring?
Yes, a hot skillet will caramelize pineapple beautifully if you don't have access to a grill, giving great flavor and grill-like marks.