It’s my birthday! So let’s celebrate with one of my favorite things: a whiskey cocktail. This one is the perfect balance of sweet, sour and strong. And it’s all extremely smooth. Meet the brown sugar pineapple whiskey sipper. A mouthful in the very best way. The title pretty much tells you what’s in it but the magic is in how it’s made. If you like whiskey and pineapple juice or spirit-forward whiskey ginger drinks, you’ll love this one. Let’s get into the details of this fabulous whiskey-based drink recipe.

pouring brown sugar pineapple whiskey sipper from cocktail shaker over ice

In case you’re new here, good whiskey cocktails are kind of my thing. Making a brown sugar pineapple whiskey sipper requires a bit of thinking ahead to make brown sugar pineapple syrup. But I know I’m worth it, especially on my birthday. And once you taste the finished drink, you’ll understand that you’re worth it, too! I highly recommend doubling or even tripling this recipe because everyone will want to enjoy more than one brown sugar pineapple whiskey sipper. It’s just such a good cocktail. As is, this recipe makes enough brown sugar syrup for two cocktails. So how exactly do you make brown sugar simple syrup? Glad you asked.

adding pineapple frond to glass to garnish whiskey cocktail

How to Make Brown Sugar Syrup

The only cooking involved in this recipe is making the brown sugar syrup. And it’s so easy, you don’t need to worry about that at all. This process is just like making simple syrup only with different ingredients. To make it, simply combine brown sugar, pineapple + pineapple juice, and a bit of ginger over heat. Let the brown sugar pineapple ginger mixture do its thing for about 20 minutes then cool. Now, you’re ready to make a couple of brown sugar pineapple whiskey sippers, boo!

two whiskey pineapple cocktails in geometric glasses

Which Whiskey to Use for this Cocktail

This is a whiskey drinker’s cocktail and made to be sipped. Hence the name. The pineapple, brown sugar, and ginger flavor notes in the syrup play well with the whiskey but by no means overpower it. So be sure to use your favorite whiskey expression. I developed this drink recipe using Uncle Nearest 1856 premium whiskey and can tell you that quality makes all the difference. This isn’t a cloying, sugary “girly” drink (whatever that means). What it is is smooth, lightly sweet, and potent. It’s not a pineapple upside down cake shot. But it’s perfect for celebrating another year of life or even just another Friday night. I know you’ll love the brown sugar pineapple whiskey sipper and highly recommend you try my whiskey champagne cocktail next–it’s also great for celebrating!

holding brown sugar pineapple whiskey sipper

In past years, I’ve celebrated with boozy baked goods like this bourbon vanilla birthday cake but am feeling a little more grown and sexy this year. Let me know how you like this brown sugar whiskey cocktail in the comments below. And sharing is caring so be sure to pin this recipe on Pinterest. Thanks for reading!

P.S. more boozy pineapple recipes:

Brown Sugar Pineapple Whiskey Sipper
Prep Time
5 mins
Cook Time
20 mins

A spirit-forward whiskey cocktail that perfectly balances sweet, sour, and smooth.

Course: Drinks
Cuisine: American
Keyword: brown sugar cocktail, brown sugar syrup cocktail, pineapple and ginger cocktail, whiskey and pinapple juice, whiskey and pineapple, whiskey cocktail with pineapple
Servings: 2 cocktails
Author: Jazzmine from Dash of Jazz
  • 1 cup pineapple chunks fresh or frozen
  • 1 cup pineapple juice
  • 1/4 cup brown sugar
  • 1 one-inch piece of ginger peeled
  • 1 ounce lemon juice
  • 4 ounces whiskey
  • ice
  1. Add pineapple chunks, pineapple juice, brown sugar, and ginger to a small saucepan over medium flame. Stir until brown sugar is dissolved then bring to a boil.

  2. Reduce heat to medium-low and simmer until mixture is reduced and slightly thickened (about 20 minutes). Remove from heat and allow to cool.

  3. To make cocktails, add ice to two rocks glasses and set aside.

  4. Add more ice, whiskey, lemon juice, and syrup to a cocktail shaker then close and shake for about 10 seconds. Pour into prepared glasses, dividing evenly.

Recipe Notes

Be sure to use a good quality whiskey (preferably your favorite) because the syrup will not drown out the flavor. The whiskey carries this drink!

whiskey cocktail over ice with text overlay "brown sugar pineapple whiskey cocktail"

holding whiskey cocktail with text overlay "pineapple ginger whiskey sipper"

pouring whiskey cocktail into glass with text overlay "pineapple & ginger whiskey cocktail"

overhead of cocktail in glass over large ice cube with text overlay "pineapple & ginger whiskey sipper"