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Who’s Your Daddy? Tiki Coffee Old Fashioned

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coffee cocktail with large pineapple garnish
Who’s Your Daddy? – Tiki Coffee Old Fashioned

It’s wildcard week for quarantine cocktails and I’m kicking it off with a cocktail that shouldn’t work but is one of the most amazing drinkable cocktails I’ve ever made – a Coffee Pineapple Old Fashioned. This shouldn’t work. I mean thinking about pineapple and coffee together doesn’t give you the warm and fuzzies. But. But. . .

You must try this.

In fact, the next time you go to a gathering, with an appropriate number of people as designated by your governor, take a batch of these along as a hostess gift to share with guests. Don’t tell them what’s it it. Just give them the name – Who’s Your Daddy – and have them guess what’s in it. They’ll be able to pick out the coffee, and maybe a little of the chocolate/coffee bitters, but I’m guessing no one will be able to identify the pineapple in it.

Pineapple and cold coffee work. They just do. In the same way that orange and coffee work, the coffee’s bitterness meets up with that sweet bold citrus and blends with it in the most delightful of ways. The slightly acidic pineapple syrup brightens and elevates the coffee’s dark and bitter notes. And it’s far too easy to sip.

coffee cocktail with large pineapple garnish
Who’s Your Daddy? – Tiki Coffee Old Fashioned

We’ve had about three days of these cocktails, and it’s a good thing pineapples are still on sale. Using an uncooked pineapple syrup is the way to go, so I’ve included that recipe in the notes below. Basically, you cover fresh pineapple with sugar and let the sugar draw out the pineapple juice and convert it to a syrup.

As far as ingredients, I used XO Café – a patron coffee liqueur to add the coffee flavor, and Crude bitters “Big Bear” coffee and cacao bitters. For whiskies, I’ve used Old Forester 100, my standby, Woodford Reserve Rye, Evan Williams single barrel, New Riff bourbon and Old Bardstown Bottled in Bond. They are all lovely, but if you want to make sure to keep that hit of bourbon on the palate, choose a bourbon that’s 100 proof or higher.

For those of you curious about the other recipes in the Quarantine Series, I’ll put them here before you skim past to get to the recipe. We had Quarantine Highball week (Highball Whiskey Spritz and a That’s No Moon Lavender Orange HighballIt Ain’t All Sunhine and Peaches, Petals to the Metal Hibiscus Highball and a Root Beer Highball. ) Quarantine Donut cocktails (Maple Caramel Long JohnPecan Sticky Bun cocktail and Blueberry Cake DonutBoston Cream Cocktail and Apple Fritter Cocktail). Quarantine Juleps, (Breakfast Julep, the Pineapple Sage Rum JulepElvis Julep (peanut butter-banana)Root Beer Float Julep, and the Persian Julep (rose-apricot) ). Quarantine Old Fashioneds (Breakfast Wakey WakeySmoke and SpiceHome SchoolTaco Truck, and Campari/Bitter Lessons ). Quarantine Manhattans (Balanced Perfection (Perfect Manhattan)Coffee ManhattanChocolate Ginger ManhattanFrench Quarter Manhattan, and the Caramel Orange Manhattan.) Quarantine Whiskey Sours (Blackberry SunsetWhiskey TikiBlue Mood OrangeYa Basic, and Peach Rosemary). Quarantine Smashes (Whiskey Smash, Blackberry Sage SmashPineapple Tiki SmashStrawberry Basil Smash and the Coffee Cherry Smash.)

coffee cocktail with large pineapple garnish
Who’s Your Daddy? – Tiki Coffee Old Fashioned
coffee cocktail with large pineapple garnish

Who’s Your Daddy? – Tiki Coffee Old Fashioned

Picture of Heather Wibbels, Cocktail Contessa, pouring a cocktailHeather Wibbels
Luscious pineapple and bitter coffee pair with bourbon for a delightful and surprising take on an old fashioned that will please bourbon newbies and fanatics alike. Coffee’s bitter notes are tamed by the pineapple syrup without overwhelming them. Everyone plays nice to make a truly sippable cocktail.
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Course Drinks
Cuisine Bourbon Cocktail
Servings 1


  • 1.5 oz bourbon 100 proof or higher
  • ¾ oz coffee liqueur
  • ½ oz pineapple syrup**
  • 16 drops Crude “Big Bear” coffee and cocoa bitters
  • Garnish: spear of pineapple cinnamon stick, coffee beans


  • Combine bourbon, coffee liqueur, pineapple syrup and bitters into a mixing glass and fill with ice. Stir until well-combined and chilled, about 30 seconds. Strain into a rocks glass with ice and garnish with a spear of pineapple.


** Pineapple syrup: cut up one small pineapple into small pieces and weigh. Weigh out the same amount of sugar and mix the two. Let sit out on a counter for 6-12 hours, or until the pineapple syrup fills up the bottom of the mixing cup. Strain and store in the fridge. If you add a splash of vodka it will keep for 3-4 weeks. Save the sweetened pineapple chunks to top an ice cream sundae or pancakes.
Batching Instructions for 8:
  • 1.5 cups bourbon
  • ½ cup pineapple syrup
  • ¾ cup coffee liqueur
  • ¾ to 1 tsp coffee and cocoa bitters
  • ½ c water
Build in an empty bourbon bottle and chill in advance. Serve on the rocks. Garnish as above.
Keyword bourbon, coffee, pineapple, tiki
Tried this recipe?Let us know how it was!
By on May 26th, 2020
Picture of Heather Wibbels, Cocktail Contessa, pouring a cocktail

About Heather Wibbels

Heather Wibbels is a whiskey and cocktail author (Executive Bourbon Steward, no less) with a passion for cocktails. She loves researching and designing cocktails, drinking cocktails, and teaching cocktails. Mostly whiskey cocktails, given her Kentucky location.

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