Ever get tired of the same boring old drinks when the sun finally comes out? Me too. That’s how I stumbled onto the pineapple old fashioned. It’s a cocktail that actually wakes up your taste buds. Regular ones can be heavy and kinda serious, but this one’s got that sweet zing of pineapple. Feels like summer in a glass, even if it’s raining outside. Trust me, it solves that “what should I sip tonight” dilemma real fast.
Pineapple Old Fashioned
Ingredients
Method
- To make the pineapple simple syrup, combine sugar, water, and chopped pineapple in a saucepan.
- Heat until sugar dissolves and pineapple is soft, about 5 minutes.
- Remove from heat, let it cool, strain out pineapple chunks, and store the syrup in the fridge.
- In a short glass, place a big ice cube.
- Pour in 2 ounces of bourbon.
- Add 3/4 ounce of homemade pineapple simple syrup.
- Add a couple of dashes of Angostura bitters.
- Stir for about 20 seconds until well mixed.
- Squeeze the strip of orange peel over the drink to release the oils, then drop it in.
- Optionally, garnish with a maraschino cherry.
Notes
What’s in a Pineapple Old Fashioned
Let’s clear this up: this is not your granddad’s usual old fashioned. The pineapple old fashioned starts with bourbon (or rye if that’s your poison), fresh pineapple simple syrup, and classic bitters. The pineapple totally changes everything. It’s sweet but not overboard. Citrus peel makes it smell good. Sometimes I’ll use orange or lemon, but I gotta say, orange is my top pick. If you want to get fancy, drop in a cherry at the end. Or don’t. Up to you.
And get this, quality bourbon really does make a difference. I mean, you don’t need to drop a paycheck, just pick something decent that you like sipping. Cheap stuff ends up, well, tasting cheap. That pineapple simple syrup? Seriously, takes like 10 minutes to make and it keeps things fresh. Some folks use store-bought syrup, but it’s just not the same. And honestly, bitters are a must. They pull things together without taking over. The sum is more than the parts if you ask me.
How to Make a Pineapple Old Fashioned (Step by Step)
Alright, here’s how it goes. First, you throw a big ice cube in your favorite short glass (I refuse to call it a ‘rocks’ glass, it’s just a cup to me). Pour in 2 ounces of your chosen bourbon. Then, add about 3/4 ounce pineapple simple syrup. Sometimes I eyeball it, but don’t judge me. A couple dashes of Angostura bitters—good old classic style—then grab your bar spoon or a regular spoon and stir.
I like to stir for a solid 20 seconds so everything mingles together. Next comes a strip of orange peel. Squeeze it over the drink so you get those zingy oils. Give the peel a twist, then toss it in. Maybe add a cherry, if that’s your vibe. That’s literally it. Drink’s ready to knock your socks off. And, ugh, it looks cool. People always ask what I’m drinking when I serve one. Not saying I’m trendy, but… you know.
“This recipe is crazy easy. Tastes like something from a five-star restaurant, so I keep making them at home for friends. Everyone’s hooked.” – Tanya from Portland
Make Homemade Pineapple Simple Syrup
Here’s the thing: pineapple simple syrup is worth it. I promise, it’s shockingly simple. You grab a saucepan, dump in equal parts sugar and water—let’s say a cup each—then add about half a cup of chopped fresh pineapple. Canned works, but it’s just not the same. Heat until the sugar melts and the pineapple gets soft, like five minutes. Let it cool. Strain out the chunks (eat ’em if you want) and store the syrup in the fridge.
Mine lasts about a week because I can’t resist throwing it in everything. Coffee, ice tea, even over pancakes once (don’t judge). Homemade always feels special, but honestly, this one’s low effort for the result. Fresh pineapple really brings a bold, tangy-sweet edge that bottled syrups just never have. Pro tip: make extra, you’ll wish you had.
Glassware for an Old Fashioned Cocktail
Let’s talk about glasses. There’s all this fuss online about “official” glassware but here’s my two cents: use what feels sturdy and looks fun. Classic old fashioned glasses are short, heavy-bottomed, and hold about 8 to 10 ounces (enough room for a big ice cube). The thick sides keep the drink cold longer and, not gonna lie, they feel good in your hand.
If you’re making drinks for a group, totally fine to mix up your glass styles. Sometimes I use fancy etched ones if I’m trying to impress. Other times, I just grab a plain glass from the cupboard. Don’t stress—your drink will still taste great. But please, the big ice cube is not optional. It chills without watering everything down at top speed. If you don’t have the fancy molds, use whatever. Even giant freezer ice will do.
More Bourbon and Whiskey Cocktail Recipes
So you liked the pineapple old fashioned? I’ve got more ideas to keep your bourbon spirits up, pun intended.
- Try making a classic old fashioned with brown sugar instead of white for an earthier flavor.
- If you like citrus, bourbon smash with lemon and mint just screams “porch weather.”
- Maple bourbon sours are sweet, tangy, and perfect for fall if you’re over pineapple but still want something cool.
- Got leftover pineapple syrup? It’s actually killer in a whiskey sour—just swap it in for simple syrup and toss in extra lemon.
Honestly, experimenting is part of the fun. Sometimes my “whoops” drinks end up beating the originals.
Common Questions
Q: Can I use store-bought pineapple juice instead of making syrup?
A: Yep, but the result will be thinner and not as punchy. Homemade syrup is much bolder.
Q: What kind of bitters work best?
A: Classic Angostura is my go-to, but orange bitters add an extra lift if you’re feeling wild.
Q: Do I have to use bourbon, or can I swap in rye?
A: Rye totally works. It’s a little spicier. Some people even use rum, but… stick with whiskey for the real vibe.
Q: How do I make a batch for a group?
A: Pre-mix everything but the ice, then pour over fresh cubes in each glass. Super easy.
Q: Is this super sweet? Will I like it if I don’t love sugary drinks?
A: It’s sweet, but you control the syrup amount. Try less at first and work up to your happy place.
Ready to Up Your Summer Cocktail Game?
Alright, so if you’re searching for a summer twist on your usual, the pineapple old fashioned is a game-changer. You can use almost everything you already have at home—plus maybe a fresh pineapple. Don’t underestimate how much homemade syrup boosts the flavor. Trust me (I’ve taste-tested a lot). Try making your own and let your friends think you’ve become some kind of cocktail genius. Give it a shot. The summer mood might just last all year.
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