Made with real vanilla beans, loads of chai spice, and smoky-sweet bourbon, these vanilla chai old fashioned cocktails deliver warmth and festivity. Perfect for crisp fall evenings!

I don't drink much lately, so when I do make the decision to indulge, it's only ever for something I reeeeally want. In summer this might be a frosty Corona with a wedge of lime or a crafty IPA in a tall glass.
As fall approaches though, my attention always drifts towards cozy cocktails.
This vanilla chai old fashioned is an autumn-inspired marriage of TWO of my favorite drinks: chai tea and bourbon! The spicy chai tea and and sweet maple-based simple syrup are the perfect compliment to the smoky, caramelized warmth of bourbon. The essential oils in the orange twist--a key ingredient in the traditional old fashioned--are enhanced by the floral vanilla beans, and the whole thing comes together into one sip that gives me all of the festive fall feels I crave.
And lest I introduce this recipe without giving bourbon a moment! A couple of years ago my boyfriend and I watched the documentary Neat (10/10 highly recommend) and promptly became bourbon people. We've tasted our way through several bottles of whiskey (I give some recs in the ingredients section below!) and have practiced making traditional old fashioneds and whiskey sours using the Viski barware I gave him as a Christmas gift last year.
To make this take on an old fashioned extra special, I use a real vanilla bean pod to infused the homemade chai syrup.
I know, I know. Vanilla beans are pricey. But like I said, my approach to drinks is quality over quantity these days, and the flavor that whole vanilla pod gives to this drink is unmatched. Plus, after it's done its work in the syrup, you can use the vanilla pod it to garnish the drinks and then dry it off and save for another use because yes, it still will have plenty of flavor left to lend.
ingredients for vanilla chai old fashioned

ingredient notes & swaps
- I love the autumnal flavor that maple syrup gives to the homemade chai syrup, so I highly recommend sticking with it. If you need an alternative, honey would work to make the chai syrup instead. Hello chai honey old fashioned!
- Cut the vanilla bean in half crosswise, then wrap the other half in a bit of plastic wrap and return it to the jar or bag it came in. It will be perfectly good to use another time.
- I have Angostura bitters at home and use it for most drinks, but there are all kinds of bitters out there to use and try. A dash orange bitters or lemon bitters would work here, and I have even seen chai spiced bitters before.
- When it comes to chai teas, use your favorite brand if you have one. I love Stash Double Spice Chai as they give a nice strong flavor. Note that chai tea uses black tea as a base so there will be some caffeine content in these cocktails. As far as caffeine free chai options, my favorite is this Yogi Honey Chai Turmeric Vitality blend.
- Same goes for the bourbon! Use your favorite brand if you have one. Bulleit Bourbon is our go to, but other favorites are Town Branch, Castle & Key, and Woodford Reserve.
vanilla chai old fashioned
Made with whole vanilla bean, loads of chai spice, and smoky-sweet bourbon, these vanilla chai old fashioned cocktails deliver warmth and festivity. Perfect for crisp fall evenings!
- Total Time: 20 minutes
- Yield: 2 drinks (plus about 1 cup extra chai syrup) 1x
Ingredients
For the Chai Simple Syrup:
- 1 cup water
- ½ cup maple syrup
- Half vanilla bean pod
- 2 chai tea bags
For Each Cocktail:
- 3-4 teaspoons homemade chai syrup (can add less or more depending on preference)
- 3 dashes bitters
- Orange twist
- Ice
- 1.5 ounces bourbon
- Vanilla bean pod halves (from making the syrup), for garnish
- Whole star anise, for garnish
Instructions
- Slice the vanilla bean half lengthwise, to produce 2 strips that are each 1 quarter of the whole pod. In a small pot over medium-high heat, bring the water and maple syrup to a low boil.
- Turn off the heat, add the vanilla bean pieces and tea bags and let steep for about 15 minutes. After the steeping is complete, remove the vanilla bean pieces and tea bags and pour the syrup into a pitcher or bottle. Reserve the vanilla bean pieces to garnish the finished cocktails and stick the tea bags in the fridge for making tea if you want! They still have some life left.
- In the bottom of an old-fashioned glass or other low, wide glass, combine 3-4 teaspoons chai syrup, a few dashes bitters, and an orange twist. Muddle a little bit to release the oils from the orange peel. I don't have a real muddler so I just use a heavy spoon!
- Add ice as desired.
- Pour the bourbon over the ice, then stir to combine it with the syrup mixture.
- Garnish each vanilla chai old fashioned with a vanilla bean piece and whole star anise. Enjoy!
Notes
- Add as much or as little chai simple syrup as you like! I go with 4 teaspoons in mine for a moderate sweetness and solid punch of chai flavor. Feel free to add less for a more bourbon-forward cocktail, or more if you want an extra sweet treat!
- If you want to make a less concentrated version of these vanilla chai cocktails, add some plain sparkling water at the end and stir once or twice to mix gently. I recommend adding just 1-2 oz of sparkling water to start. Keep in mind the ice will melt and mellow the flavors out as well.
- Prep Time: 5 minutes
- Steeping Time: 15 minutes
- Category: drinks
- Method: stirred
- Cuisine: cocktails
FAQs
How Do I Store the Extra Syrup?
Pour your leftover chai tea simple syrup into a bottle (I usually save a few cleaned maple syrup bottles for things like this!) or other airtight container and keep it in the fridge. Due to the sugar content, it should last for up to a month.

Looking for other festive fall recipe ideas? 🍂 Try my Roasted Cauliflower and Pumpkin Soup or Pumpkin Spice Blondies for dessert.
dig in!
Enjoy & let me know what you think 🌙 💛










