13 Most Popular Pineapple Bourbon Cocktails to Try

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.