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13 Most Popular Pineapple Bourbon Cocktails to Try

Experience the perfect blend of sweet and smoky with pineapple bourbon cocktails. These delightful libations expertly combine the rich, caramel notes of bourbon with the tropical, tangy essence of pineapple, creating a refreshing and flavorful drink that’s sure to captivate both bourbon aficionados and fruit cocktail enthusiasts alike.

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Whether you’re a mixology maven eager to craft new concoctions or simply someone who enjoys exploring unique flavor pairings, pineapple bourbon cocktails offer an exciting option for those seeking a delicious twist on classic bourbon-based libations. So, grab your cocktail shaker and get ready to elevate your sipping experience!

Bourbon Pineapple Smash

Bourbon Pineapple Smash
source: jennifermeyering.com

Indulgent, fruity, and spirited, this cocktail boasts a harmonious blend of robust bourbon and tropical pineapple. With each sip, you’ll be greeted by the rich, caramel notes of the bourbon, perfectly complemented by the vibrant sweetness of fresh pineapple. Serve it over crushed ice and garnish with a pineapple wedge for a true smash experience. Ideal for unwinding after a long day or as a lively companion at backyard BBQs and rooftop soirées.


Pineapple Bourbon Punch

Pineapple Bourbon Punch Recipe
source: lemonsforlulu.com

This vibrant punch combines the mellow allure of bourbon with the sunny embrace of pineapple. Prepare to be enchanted by its balanced flavors—sweet pineapple dances with the warm, oaky undertones of bourbon, creating a harmonious medley. To savor this punch at its finest, fill a punch bowl with ice, add the pineapple-infused bourbon, fresh fruit slices, and a splash of soda water. Perfect for sharing with friends at laid-back gatherings or festive celebrations.


Pineapple Bourbon Mule

Pineapple Bourbon Mule
source: offthelinecooking.com

Bold, zesty, and utterly irresistible, the Pineapple Bourbon Mule adds a tropical twist to the classic cocktail. This spirited concoction features the delightful combination of bourbon, tangy pineapple juice, zingy ginger beer, and a splash of lime. Serve it in a copper mug filled with ice, garnished with a pineapple wedge and a sprig of mint. Unleash your adventurous side and enjoy this refreshing drink during summery rooftop parties or lively game nights.


Pineapple Old Fashioned

Pineapple Old Fashioned
source: thelittlestcrumb.com

Experience a fusion of timeless sophistication and exotic flavors in the Pineapple Old Fashioned. The classic cocktail receives a tropical makeover as smooth bourbon mingles with the sweet tanginess of pineapple and a hint of aromatic bitters. Serve it over a large ice cube in an old-fashioned glass, garnished with a pineapple leaf for a touch of elegance. This captivating blend is perfect for intimate evenings, upscale cocktail lounges, or when you’re in the mood for a refined indulgence.


Wicked Behavior

Wicked Behavior
source: imbibemagazine.com

Prepare for a sinfully delightful journey with the Wicked Behavior cocktail. Blending the spiciness of bourbon, the lusciousness of pineapple, and the allure of secret ingredients, this mysterious concoction is equal parts naughty and nice. Basking in a chilled coupe glass, this seductive drink is best enjoyed at intimate speakeasies, sultry cocktail lounges, or when you’re feeling a bit rebellious and want to add a touch of wickedness to your night.


Pineapple Bourbon Sour

Pineapple Bourbon Sour
source: gigglesgobblesandgulps.com

Embrace the tangy and tart allure of the Pineapple Bourbon Sour. With a tantalizing balance of bourbon, zesty pineapple juice, and a touch of lemon, this cocktail is a burst of vibrant flavors. Shake it with ice, strain into a rocks glass, and garnish with a pineapple slice to elevate its visual appeal. Whether you’re sipping it at lively rooftop parties or unwinding after a long week, this lively drink is sure to leave your taste buds craving more.


Bourbon Bird

Bourbon Bird
source: boozeontherocks.com

Take flight with the Bourbon Bird, a cocktail that combines the smoothness of bourbon with the tropical charm of pineapple. This delightful elixir reveals layers of flavor, from the rich caramel notes of bourbon to the juicy sweetness of pineapple. Best enjoyed in a highball glass over ice, garnished with a pineapple spear, it’s the perfect companion for laid-back beach gatherings, garden brunches, or simply when you want to add a touch of sunshine to your day.


Hibiscus Pineapple Bourbon Cocktail

Hibiscus Pineapple Bourbon Cocktail
source: anothercocktailblog.com

Immerse yourself in a tropical paradise with the Hibiscus Pineapple Bourbon Cocktail. Infused with the essence of hibiscus, this spirited drink marries the deep, complex flavors of bourbon with the vibrant tanginess of pineapple and a subtle floral undertone. Served in a chilled martini glass, garnished with a pineapple leaf, it’s an exquisite choice for garden parties, upscale lounges, or when you want to transport your senses to an enchanting island escape.


Twisted Painkiller

Twisted Painkiller
source: nooneleaveshungry.com

Get ready for a blissful twist on a classic cocktail with the Twisted Painkiller. Combining the velvety smoothness of bourbon with the tropical allure of pineapple and a touch of coconut, this drink offers a harmonious blend of flavors. Shake it with ice, strain into a tiki glass, and garnish with a pineapple wedge and a cherry to enhance its visual appeal. Perfect for summer parties, poolside lounging, or when you’re in the mood for a vacation in a glass.


Pineapple Whiskey Smash

Discover the bold fusion of whiskey and pineapple in the Pineapple Whiskey Smash. This crowd-pleasing cocktail blends the robustness of whiskey with the juicy tang of pineapple, creating a spirited and captivating experience. Muddle pineapple chunks with whiskey, add a squeeze of fresh lime juice, and serve it over crushed ice in a rocks glass. Enjoy it during lively outdoor gatherings, rooftop celebrations, or whenever you’re seeking a bold and flavorful drink.


Hawaiian Stone Sour

Hawaiian Stone Sour
source: realhousemoms.com

Transport yourself to the enchanting islands of Hawaii with the Hawaiian Stone Sour. This delightful cocktail combines the smoky allure of bourbon with the vibrant sweetness of pineapple and the zesty tang of citrus. Shake it with ice, strain into a highball glass, and garnish with a pineapple wedge and a cherry for a tropical touch. Sip on this paradise-inspired drink during beach parties, luau-themed gatherings, or when you’re yearning for a taste of aloha.


Pineapple Bourbon Fizz

Pineapple Bourbon Fizz
source: boozybodybuilder.com

Sparkling, playful, and utterly satisfying, the Pineapple Bourbon Fizz is a cocktail that combines the lively bubbles of soda with the tropical delight of pineapple and the smoothness of bourbon. Shake bourbon, pineapple juice, and a splash of lemon juice with ice, strain into a tall glass, and top with soda water. Garnish with a pineapple slice for an extra pop of flavor. Whether you’re lounging by the pool or hosting a brunch, this fizzy drink is a crowd-pleaser.


Pineapple Bourbon Lemonade

Pineapple Bourbon Lemonade
source: cheesecurdinparadise.com

Sweet, tangy, and stimulating, the Pineapple Bourbon Lemonade is a perfect balance of flavors. This delightful fusion features the robust warmth of bourbon, the zesty freshness of lemonade, and the tropical sweetness of pineapple. Shake bourbon, pineapple juice, and freshly squeezed lemonade with ice, strain into a glass filled with crushed ice, and garnish with a lemon wheel. Ideal for picnics, backyard barbecues, or when you’re craving a sunny and uplifting sip.


A Bourbon Pineapple Smash cocktail, featuring a mix of bourbon and pineapple juice, garnished with a pineapple wedge and mint leaves. The drink is in a short glass, on a dark wood surface. Soft lighting casts a warm glow on the cocktail, highlighting the rich amber color of the bourbon and the vibrant green of the mint. The background is softly blurred, focusing attention on the drink.

13 Pineapple Bourbon Cocktail Recipes

Prep Time: 5 minutes
Total Time: 5 minutes
4.7 from 3 votes
Course: Drinks
Cuisine: American
Keyword: pineapple bourbon cocktails
Servings: 1
Author: Paul Kushner
Elevate your mixology skills with tantalizing pineapple bourbon cocktails.

Instructions

  • Pick your favorite recipe
  • Gather all the needed ingredients
  • Prep a pineapple bourbon cocktail in less than 5 minutes
Tried this recipe?Leave a comment and let us know how it was!
13 Most Popular Pineapple Bourbon Cocktails to Try
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Paul Kushner

Written by Paul Kushner

Founder and CEO of MyBartender. Graduated from Penn State University. He always had a deep interest in the restaurant and bar industry. His restaurant experience began in 1997 at the age of 14 as a bus boy. By the time he turned 17 he was serving tables, and by 19 he was bartending/bar managing 6-7 nights a week.

In 2012, after a decade and a half of learning all facets of the industry, Paul opened his first restaurant/bar. In 2015, a second location followed, the latter being featured on The Food Network’s Diners, Drive-Ins and Dives.

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