Cherry Chai Manhattan

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(Note: this post was originally published on December 12, 2019. It has since been updated with a few tweaks.)

A Cozy Chai Manhattan for Cold Winter Nights

Faced with short days, cold temperatures, and gray skies, I think we all might be in need of a special cocktail. Never fear, this unique Cherry Chai Manhattan is here to make those chilly nights feel a little bit cozier. It's boozy, seductive, complexly flavored, and subtly earthy; perfect for unwinding on a cold, dark winter evening.

Although this spicy cherry Manhattan riff doesn't require many ingredients, the flavors are very complex and unique. The bourbon brings notes of vanilla, oak, and even fruit. Chai bitters add depth of flavor and subtle spiciness, while cinnamon syrup adds warming notes and a bit of sweetness. Finally, Luxardo (an Italian cherry liquor) adds the richness and earthiness of cherries.

This simple winter / Valentine's Day bourbon cocktail is a date night staple in our house. I hope you enjoy it as much as we do!

Elegant Cherry Chai Manhattan cocktail in a coupe glass, shown with mixology bottles and jars in the background

How to Make a Simple Syrup

This cozy chai Manhattan relies upon a simple syrup to get all that wonderful cinnamon flavor into a drinkable form. If you've never made a simple syrup before, don't let the name intimidate you. It's easy to do at home and a simple syrup keeps great in the fridge for weeks.

A simple syrup is just a 1:1 mixture of sugar and water, cooked down until it becomes thick and syrupy. It's a great way to capture flavors that are difficult to get into a liquid form otherwise. Because cinnamon is a solid, you can't readily add it to a cocktail; it won't dissolve. That's why simple syrup is a very powerful tool in mixology.

The recipe below will walk you through making a cinnamon simple syrup using whole cinnamon sticks. But this concept will work for just about anything you can dream up, so don't be afraid to experiment. Herbs, other warming spices, and edible flowers all yield wonderful simple syrups. You can use this cinnamon simple syrup in other cocktails too, including this unique Cinnamon Cherry Paloma or even just a simple Old Fashioned.

Two Cherry Chai Manattan cocktails for Valentine's Day shown with cinnamon sticks, chai bitters, a jar of cherries, and a barspoon

Cherry Chai Manhattan Variations

Although this cocktail isn't a traditional Manhattan, that term is still probably the best descriptor of its flavors and format. A classic Manhattan is typically rye (although bourbon is also common), vermouth, and bitters, stirred and served straight-up in a coupe or martini glass, often garnished with a Luxardo cherry. This Manhattan riff swaps Luxardo liqueur for the vermouth and uses chai bitters instead of the more typical Angostura, plus it incorporates a barspoon of the Luxardo cherry syrup and a little bit of cinnamon simple syrup for a kiss of sweetness.

This chai + cherry Manhattan is designed to be a small-format, strong cocktail. That said, if you have guests who would appreciate a larger-format cocktail, you can always serve it on the rocks (more like an Old Fashioned). It even works with a splash of ginger beer, similar to how I serve this Tom and Cherry Aged Gin Cocktail. If you're hosting, try making them to-order so that everyone can get a drink that works for them.

If you don't have or can't find chai bitters, this Valentine's Day bourbon cocktail can still work. If possible, use something with wintry spices like cinnamon bitters (although really, any bitters will work alright). Or, you can also make a chai simple syrup (instead of the cinnamon simple syrup as written) using loose-leaf chai tea. This small-format cocktail won't work with actual chai tea, but check out this Chaider Rum Punch or this Chai Tai if you're looking for a cocktail that incorporates brewed tea.

Close-up of a Cherry Chai Manhattan bourbon cocktail, garnished with a cocktail cherry

Ingredients and Substitutions

Here's what you'll need for this spicy cherry Manhattan recipe, as well as some thoughts, tips, and possible substitutions. If you make any substitutions, I'd love to hear about it in the comments section below.

  • Cinnamon sticks. This won't work with cinnamon powder.
  • White sugar.
  • Bourbon. In a small, strong drink like a Manhattan, using a quality bourbon is key. I like to mix this one with something solidly middle-shelf like Knobb, Bulleit, or equivalent. You can also use rye, which is common in a Manhattan.
  • Luxardo liqueur. This fabulous Italian liqueur is the flavor powerhouse in this cherry Manhattan. There isn't a great substitution, so I highly suggest getting your hands on a bottle of this liquid gold.
  • Luxardo syrup. This is the magical syrup that surrounds the Luxardo cherries in the jar. Luxardo cherries are a splurge purchase, but they make this wintery / Valentine's Day bourbon cocktail feel so special.
  • Chai bitters. Or use any other bitters you have on-hand, although you'll lose some of the chai flavor. See the section above for other options, including a chai simple syrup.
  • Luxardo cherry

Low-angle view of a Manhattan Valentine's Day bourbon cocktail, showing the beautiful deep-red color

Closing Thoughts

Isn't this such a special, decadent pairing of flavors? Something about the sweet and earthy cherry, cozy bourbon, and warming spices just feels so luxurious. And luxury is absolutely what you deserve on a chilly winter Friday evening after a long week! I love that this chai Manhattan is a grown-up, evening-appropriate, party-worthy way to enjoy the flavors of the traditional tea.

We've really fallen in love with this chai + cherry Manhattan; it has been a date night staple in our house for years. There's nothing better than sipping one of these in front of the fireplace on a dark evening, when you need a little warming from both the inside and the outside. Or perhaps a Valentine's Day bourbon cocktail is on the menu for your celebration this year??

Simple view of an elegant chai Manhattan in a coupe glass against a white background, garnished with a cocktail cherry

Share It!

It makes me so happy to hear from you and see your creations! Please leave a comment below and let me know what you think about this recipe. If you post a photo on Instagram, hashtag #TheRogueBrusselSprout and tag me (@TheRogueBrusselSprout) in the post text so that I'm sure to see it.

As with all my cocktail recipes, please enjoy responsibly!

Suggested Pairings

Maple Sea Salt Hummus

Orange and Cinnamon Roasted Delicata Squash

Vegan Brussels Sprouts Waldorf Salad

Creamy Vegan Kabocha Squash Soup with Fall Herbs

Chai-Spiced Pear Crumble Bars

Cherry Chai Manhattan

A seductive winter sip, this chai Manhattan unites bourbon with sweet cherry and cozy spices. It's perfect for a chilly evening and especially for Valentine's Day.

Author:
Lee

Ingredients

For the Cinnamon Simple Syrup

  • 6 whole cinnamon sticks
  • 1 c water
  • 1 c granulated white sugar

For the Cocktail

  • 2 oz high-quality bourbon
  • 0.5 oz Luxardo liqueur
  • 0.25 oz cinnamon simple syrup
  • Barspoon of Luxardo cherry syrup
  • Few dashes of chai bitters
  • Luxardo cherry

Instructions

  1. To make the cinnamon simple syrup, combine the cinnamon sticks with the water and sugar, bring to a boil, and then reduce to a low boil. Boil until the mixture has reduced significantly and turned a light amber color. It should be thick enough to coat the back of a spoon.
  2. Strain the simple syrup through a fine-mesh sieve to remove any wayward cinnamon stick bits.
  3. Put the simple syrup in a jar or container and chill it for several hours.
  4. To make the cocktail, combine everything except the cherry in a cocktail stirring glass, then stir well with ice.
  5. Strain into a chilled coupe glass and garnish with a Luxardo cherry.

Leave a Comment

Please Share Your Thoughts!

Did you make this recipe? Did you make substitutions? How did you serve it? Any helpful tips? Please share your thoughts, since these insights are really useful to both me and to other readers.

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Joanne
February 15, 2025
Oh wow! What a great recipe. A Manhatten is such a great, cozy drink. I'm thinking of jazz clubs or winter nights by the fire with one of these delicious drinks!
Lee
February 2, 2023
Kacie- You're in for a treat, Luxardo is special. Most well-stocked liquor stores will have it. You'll want to look near the liqueuers; it's often near Grand Marnier, Contreau, etc. Luxardo makes a few different products, but you just want to classic. It's in a tall, green bottle with a wood(ish) base. It's middle-range in terms of price, but you don't use much at once, so a bottle will last you a long time. Hope that helps!
Kacie
February 2, 2023
How do I find Luxardo I'm not sure I've seen it before?
Eric
January 26, 2021
We made these on a cold January weekend. Used regular bitters since we couldn't find chai. We meaning my wife especially enjoyed how the extra sweetness made this cocktail feel less intense then a classic manhattan.