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Killer Tropical Chai Highball

5 from 2 votes

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chai highball with cinnamon stick, pineapple, orange and pineapple frond garnish
Chai Highball

Greet winter in highball form with this Chai Highball. Rather than holding out for yet another warm whiskey drink, I’m switching to chai-infused whiskey, tropical syrups and a touch of spicy bitters to build up the flavor profile of this approachable highball. With each sip you get a lovely combination of winter spice from the highball and citrus tickles from the carbonated orange soda. 

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Chai-infused Highball

To make this chai-infused highball, we’ll infuse the bourbon for about 10 minutes with a bag of hot chai tea and then let it sit for about a week to deepen in flavor. Don’t worry, you won’t regret the wait. While initially there will be some great chai flavors, giving the infusion some time to settle and deepen is the key to taking this highball from tropical flavors to feeling like a winter tipple.

What’s in a Highball?

A highball is a blissfully simple cocktail in its most basic form. A highball usually consists of a bit of whiskey, and a touch of carbonated seltzer or soda. If you’ve ever ordered a seven and seven you’ve had a variation of the highball with Seagram’s 7 and Seven-up.  In their classic form they are simple to make, but are designed to highlight the flavor of the whiskey in a refreshing and wholly approachable drink.

Chai-infused Spirits

chai highball with cinnamon stick, pineapple, orange and pineapple frond garnish
Chai Highball

To infuse any spirit, you’ll just take a bag of chai tea, quickly dip it in hot water, then steep in the spirit for about 10 minutes, and no longer than 15. With tea infusions, if the tea bag is not 100% herbal and contains black, green or white tea, the tea itself dries out the spirit – adding tannic notes and contributing to a drier and less creamy mouthfeel.

Because we want to retain the lovely mouthfeel of the whiskey we’ll use, we only infuse for under 15 minutes when using a tea with green, black or white tea leaves in it. Any longer than that and you risk a pucker in the final version of the spirit.

For a tea infusion, I find it helpful to do the initial infusion, then wait 10-14 days for the flavor to deepen in the spirit. I learned this through experimentation. The infusion was good the first day, but at 10 days, it was heaven in a glass. So let it rest if you have time.

Tropical Flavors in a Winter Drink

It’s the middle of December, but I love the combination of chai tea and pineapple flavors. In addition, I’m using the Franklin and Son’s Mandarin Mixer available at Fresh Market. It’s a British product just now making its way across the pond, and the mandarin citrus notes from this carbonated soda add the fragrance of dried orange peel to the highball, tying in a lovely way with the citrus, cinnamon and cardamom flavors. 

While I was given this mixer as a sample by Franklin and Son’s, I do enjoy the intriguing taste of this citrus flavored mixer, and when combined with the flavor of a chai infusion it’s a lovely drink.

To build on those citrus flavors, I used a homemade pineapple syrup and just a small amount of lemon simple syrup. But to really punch up the flavors I added cardamom bitters from Scrappy’s Bitters, and a Pineapple Serrano Bitter from JD Bittering in Louisville. The two pulled down the sweetness of the mixer and simple syrups and tied well to the spice infusion of the chai tea in the whiskey.

How to Make the Chai Highball

chai highball with cinnamon stick, pineapple, orange and pineapple frond garnish
Chai Highball

We’ll make this so easy you can build in the glass. Add 1.5 oz chai-infused whiskey, ½ oz pineapple syrup and a dash of lemon simple syrup. Add in 3 dashes of the pineapple serrano bitters and 12 dashes of the cardamom bitters and stir briefly after adding ice.

Other Highballs You Might Enjoy

Recommended Bar Tools

You don’t need every slick, beautiful bar tool out there, but there are several I’ll recommend. (As an Amazon Associate I earn from qualifying purchases. However, that does not affect the cost of the items below.) My favorite pieces usually come from the Cocktail Kingdom section of Amazon:

You may already have these bar essentials, but just in case:

chai highball with cinnamon stick, pineapple, orange and pineapple frond garnish

Chai High

Picture of Heather Wibbels, Cocktail Contessa, pouring a cocktailHeather Wibbels
Let the flavors of winter explore a summer feel with this chai-infused whiskey highball featuring pineapple syrup, lemon syrup, cardamom bitters and pineapple bitters. Topped off with a mandarin mixer from Franklin and Sons from Britain you won’t mind the ice in December.
5 from 2 votes
Course Drinks
Cuisine Bourbon Cocktail
Servings 1


  • 1.5 oz chai-infused whiskey
  • ½ oz pineapple syrup**
  • 1/4 oz lemon simple syrup***
  • 12 drops Scrappy’s cardamom bitters
  • 3 dashes JD Bittering Pineapple Serrano bitters
  • 4-6 oz Franklin & Sons Mandarin Mixer
  • Garnish: dried orange pineapple. Cinnamon stick, star anise


  • Combine whiskey, pineapple syrup, lemon syrup and bitters in a rocks glass half filled with ice. Stir. Add more ice and top with the orange flavored mixer. One quick stir with a spoon then garnish as desired.


** 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.
***Lemon Simple Syrup:
  • 3/4 cup lemon juice
  • 3/4 cup sugar
  • Peels from the fresh lemons you just juiced – just the peel, no pith
Combine the juice and sugar in a small saucepan on medium heat, stirring until the sugar is dissolved and it’s at a very low simmer. Add the lemon peels, stir, and let sit for about 5 minutes on low heat. Turn off the heat and let the whole mixture steep for 45 minutes. Strain out the peels, bottle and refrigerate the lemon simple syrup. It will keep about 2 weeks, a little longer if you add some vodka to it.
Keyword chai spice, highball, lemon, mandarin orange, pineapple
Tried this recipe?Let us know how it was!
By on December 17th, 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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