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Top 13 Grapefruit Bourbon Cocktails to Drink

Step into the vibrant world of grapefruit bourbon cocktails, where the zesty allure of grapefruit meets the smooth embrace of bourbon. Imagine the perfect marriage of citrusy brightness and the rich, caramel undertones of bourbon, creating a libation that’s both invigorating and comforting. Whether you’re a seasoned aficionado looking to expand your palate or someone seeking a lively introduction to the world of cocktails, these grapefruit-infused delights are tailor-made for anyone ready to embark on a spirited journey of taste and indulgence.

Brown Derby

Boozy Refreshing Brown Derby Cocktail with Bourbon and Grapefruit

The Brown Derby cocktail, a delightful combination of bourbon, fresh grapefruit juice, honey syrup, and a twist of grapefruit peel for garnish, offers a captivating blend of flavors. With a smooth and rich character from the bourbon, the tangy and citrusy notes of the grapefruit juice complement it perfectly. The addition of honey syrup adds a touch of sweetness, harmonizing the elements. Served chilled and strained into a classic cocktail glass, this drink embodies sophistication. Its balanced and refreshing profile makes it an ideal choice for those seeking a nuanced cocktail experience. 

Grapefruit Bourbon Smash

Grapefruit Bourbon Smash garnished with a grapefruit wedge and a mint sprig.

The Grapefruit Bourbon Smash cocktail combines a medley of enticing flavors to create an unforgettable drink. A sugar cube adds a touch of sweetness, enhancing the overall taste profile. Medium-large mint leaves infuse a herbaceous note, while fresh grapefruit provides a zesty citrus burst. The addition of fresh grapefruit juice amplifies the fruity essence, perfectly balanced by the robust depth of bourbon. When mixed together, these ingredients harmonize into a tantalizing blend of sweet, tangy, and herbaceous flavors. Elevate your cocktail game and indulge in the Grapefruit Bourbon Smash, a captivating concoction that will leave your taste buds craving more. Cheers to a citrus-infused adventure!

Grapefruit Bourbon Sour

Grapefruit Bourbon Sour Garnished with grapefruit peel.

Originating from the classic cocktail era, the Grapefruit Bourbon Sour is a sensational drink that tantalizes the taste buds. Crafted with Coopers’ Craft bourbon, Bitter Orange Liqueur, grapefruit juice, lime juice, cinnamon syrup, egg white, and a dash of salt, this cocktail delivers a harmonious blend of flavors. The bourbon provides a smooth and robust foundation, while the Bitter Orange Liqueur adds a delightful citrus twist. The grapefruit and lime juices offer a stimulating tartness, complemented by the subtle warmth of cinnamon syrup. The egg white lends a silky texture, creating a velvety mouthfeel. This delightful concoction has gained popularity for its complex yet balanced flavor profile, making it a go-to choice for cocktail enthusiasts seeking a sophisticated and satisfying drink.

Old Fashioned Paloma

Old Fashioned Paloma Garnished with grapefruit and a sprig of fresh mint.

The Old Fashioned Paloma cocktail effortlessly combines the timeless elegance of an Old Fashioned with the vibrant zest of a Paloma. Made with bourbon, Angostura bitters, and grapefruit soda, this drink strikes a delightful balance between richness and refreshment. Simple to serve, it requires just a few ingredients and minimal preparation. The Old Fashioned Paloma appeals to a wide range of palates, offering a versatile option for both whiskey enthusiasts and those who prefer lighter, citrus-forward drinks. Enjoy it over ice, savoring the mingling flavors as the bourbon and bitters harmonize with the fizz of the grapefruit soda, creating a captivating and enjoyable drinking experience.

Bourbon Grapefruit Sidecar

Bourbon Grapefruit Sidecar garnished with a half of a thin grapefruit slice.

Indulge in the enticing allure of the Bourbon Grapefruit Sidecar, where bold flavors harmonize to create a remarkable drink. The smooth and robust bourbon entwines with the vibrant orange liquor, forming a delightful marriage of richness and citrus brightness. Fresh grapefruit juice adds a tangy and stimulating twist, while the garnishes of grapefruit zest, sugar, and a slice provide an aromatic and visually appealing touch. The garnishes of grapefruit zest and sugar enhance the aromatics and add a touch of visual elegance, while the grapefruit slice offers a juicy and decorative element. From the first sip to the last, let the harmonious blend of bourbon, orange liquor, and fresh grapefruit juice transport your taste buds to a realm of exquisite pleasure. 

The Mint Fedora

The Mint Fedora garnished with a Mint leaves and grapefruit slices.

Introducing the Mint Fedora Cocktail, a tantalizing blend of flavors that will transport your taste buds to new heights. With a twist of grapefruit juice, the rich depth of bourbon, the invigorating essence of homemade mint simple syrup, and a touch of Elemakule Tiki Bitters. This drink offers a harmonious balance of citrus, herbal, and smoky notes. The mint leaves and grapefruit slices garnish add a visual and aromatic appeal, enticing you to indulge in this captivating concoction. Sip on this delightful elixir and let it transport you to a tropical paradise, where the zesty grapefruit, fragrant mint, and smooth bourbon blend together in perfect harmony.

Pink Grapefruit Bourbon Crusta

The Pink Grapefruit Bourbon Crusta cocktail combines the smooth richness of bourbon with the delicate sweetness of Luxardo maraschino cherry liqueur, Triple Sec, and pink grapefruit juice. 

Pink Grapefruit Bourbon Crusta garnished with large section of grapefruit peel.

The addition of simple syrup and bitters adds a subtle balance of sweetness and complexity to the mix. While the pink grapefruit juice and granulated sugar rim enhance the citrusy tang and provide a touch of sweetness. This cocktail is commonly served in a cocktail or coupe glass, allowing the vibrant pink hue to shine through. A delightful medley of flavors will greet you when you take a sip. This cocktail is perfect for sophisticated evenings, adding a touch of sophistication to cocktail parties, intimate gatherings, or even a nightcap by the fireplace. Cheers to memorable moments and tantalizing sips!

The Third Man Cocktail

The Third Man Cocktail garnished with a grapefruit twist.

The Third Man Cocktail is a unique blend of bourbon, grapefruit juice, lemon juice, Campari, and simple syrup, setting it apart from other traditional bourbon cocktails. The combination of grapefruit and lemon juice adds a citrus twist, while Campari contributes a subtle bitter complexity, creating a harmonious medley of flavors that perfectly complement the smoothness of bourbon. This cocktail is typically served chilled, allowing the flavors to mingle and develop. Each sip of The Third Man Cocktail is a stimulating and invigorating journey for the taste buds. Perfect for any occasion, this cocktail is a choice that will leave you longing for more. Cheers to the intriguing flavors and memorable moments that this enticing drink brings!

Grapefruit Bourbon Spritz

Grapefruit Bourbon Spritz

The Grapefruit Bourbon Spritz cocktail offers a delightful combination of flavors that dance on the palate. With the refreshing tang of fresh pink grapefruit juice and lemon juice, the smooth depth of bourbon, and the subtle warmth of ginger simple syrup, each sip is a harmonious blend of citrus, sweetness, and spice. The addition of a splash of club soda adds a gentle effervescence, elevating the drink’s refreshing qualities. It can be enjoyed as a pre-dinner aperitif or as a relaxing sipper during social gatherings. The Grapefruit Bourbon Spritz is beloved for its invigorating flavors, well-balanced composition, and ability to evoke a sense of joy and conviviality.

Bourbon Grapefruit Punch

Bourbon Grapefruit Punch garnished with a few mint sprigs.

The Bourbon Grapefruit Punch cocktail combines a medley of flavors that contribute to an unforgettable drink. With the smooth and rich flavor of bourbon, the pink grapefruit juice provides a vibrant and tangy citrus base. The angostura bitters add a touch of complexity and depth, while the club soda provides a refreshing fizz. The mint simple syrup lends a stimulating and herbaceous note, adding a touch of sweetness. With its enticing blend of flavors, the Bourbon Grapefruit Punch is a must-try cocktail that promises to elevate any gathering or celebration. Raise your glass and indulge in the invigorating symphony of tastes that this captivating concoction offers. 

Old Fashioned Maple Brown Derby

Old Fashioned Maple Brown Derby

The Old Fashioned Maple Brown Derby cocktail delights with its unique combination of flavors. The smooth bourbon pairs harmoniously with the tangy grapefruit juice, while the rich maple syrup adds a delightful sweetness. Bitters provide a hint of complexity, and the maraschino cherry adds a touch of garnish. Originating from the classic Brown Derby cocktail, this variation gained popularity for its intriguing blend of bourbon, citrus, and maple undertones. Served over ice, it has become a beloved choice for those seeking a sophisticated and satisfying drink.

Sage Brown Derby

Sage Brown Derby

The Sage Brown Derby cocktail is a delightful drink that is both simple to serve and versatile in its appeal. With whiskey, red or pink grapefruit juice, fresh lime juice, agave syrup, bitters, and a fresh sage leaf, it can be easily prepared by mixing the ingredients together. This drink offers a balanced combination of flavors, making it suitable for a wide range of palates. To enjoy, simply pour the cocktail over ice, garnish with a fresh sage leaf, and savor the harmonious blend of whiskey, tangy grapefruit, zesty lime, subtle sweetness from agave syrup, and the aromatic touch of sage. Whether you’re hosting a gathering or simply unwinding after a long day, the Sage Brown Derby cocktail is a refreshing and enjoyable choice for all.

Charred Grapefruit Cocktail

Charred Grapefruit Cocktail

Indulge in the enticing Charred Grapefruit Cocktail, a tantalizing drink that brings together a harmonious blend of flavors. The smoothness of bourbon intertwines with the smoky essence of charred grapefruit juice, creating a rich and intriguing taste. The honey-thyme simple syrup adds a delightful sweetness, perfectly complementing the tangy notes of the grapefruit. Combined, these ingredients form a captivating cocktail that is both delightful and satisfying. Served over ice and garnished with a strip of grapefruit zest, this drink offers a visually appealing presentation that enhances the overall experience. Unleash your taste buds and embark on a sensory journey with the Charred Grapefruit Cocktail. Whether you’re enjoying a relaxing evening at home or hosting a gathering, this cocktail is sure to impress and delight.

A Grapefruit Bourbon Cocktail in a classic old-fashioned glass, placed on a vintage bar counter. The cocktail is a subtle pink hue, resulting from the mix of fresh grapefruit juice and bourbon, and is garnished with a grapefruit slice and a maraschino cherry. The glass has a thick base, characteristic of old-fashioned glasses. The background features an old-world bar ambiance with rich, dark wood, antique decor, and shelves stocked with various bourbon bottles.

13 Grapefruit Bourbon Cocktail Recipes

Yield: 1
Prep Time: 5 minutes
Total Time: 5 minutes


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Top 13 Grapefruit Bourbon Cocktails to Drink
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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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