Grapefruit Bourbon Sidecar

A member of the sours family, the Bourbon Grapefruit Sidecar features the bright colors of grapefruit juice against a sugared rim with grapefruit zest.  A cousin of the classic Sidecar, this grapefruit forward concoction stars at brunch, but works nicely at happy hour to relax and refresh after a hot day.

While working through this recipe, we found a dash of rich demerara syrup or just a pinch of demerara sugar worked wonders in balancing out the tart-forward grapefruit base.  That said, not every drink is for everyone.  As this cocktail leans heavily to the sour side, upping the sugar a bit gained nods of approval from our tasters, but those who loved this drink also enjoy grapefruit in general.  Finally, several tasters commented that as they drank the Grapefruit Bourbon Sidecar, they enjoyed it more and more.


Swapping the base bourbon reveals exciting nuances to the drink.  However, for the orange liquor, we do not recommend anything other than Cointreau.  Garnish options range from grapefruit to orange, using wheels or wedges to vary your presentation.  Also, the sugared rim lends itself to further variation.  Prepare to adjust and explore to find your perfect version.

As touched on earlier, adjusting the sugar ratio improves the drink for some.  The sweetener in this drink, Cointreau, at 40% ABV, contributes to this boozy, very dry drink.  As a result, adding a bit of sweetness in the form of rich demerara syrup proves a welcome addition for many drinkers.  Grapefruit juice ranges from sweet-tart to very sour, so combat an overly tart taste by swapping variations of grapefruit juice.  Options like white, pink, and ruby red grapefruit juice change both the drink’s color and sour to sweet balance so experimentation with the base ratio becomes necessary.

Reader Challenge

Many of us who experiment with recipes know well the frustration of feeling like a cocktail remains just short of perfection.  As much as we loved the Grapefruit Bourbon Sidecar, our tasters all agreed the drink is missing something capable of turning this into a wow-drink.  Please let us know if you unlock the missing link in this impressive, but not yet fully realized cocktail as presently this drink is somehow held back from reaching its full potential.

Grapefruit Bourbon Sidecar

Prep Time 10 mins
Course Cocktail
Servings 1


  • Small bowl
  • A small plate for creating the sugar rim
  • Grater
  • Coupe glass
  • Japanese jigger
  • Shaker
  • Hawthorne strainer




  • 2 oz bourbon
  • ¾ oz Cointreau
  • ¾ grapefruit juice
  • 1 dash of demerara syrup
  • ice


Sugar rim & garnish

  • Mix grapefruit zest with the demerara sugar, and spread it onto a small plate evenly. The sugar layer should be about ¼ of an inch thick.
  • Fill a small bowl with water. Dip the rim of a coupe glass about ½ of an inch deep into the water. Then dip the glass into the sugar and zest mixture to coat the rim.
    Grapefruit Bourbon Cocktail With Grapefruit Zest And Demerara Sugar Coated Rim

The cocktail

  • Add bourbon, Cointreau, a dash of demerara syrup, and the grapefruit juice to the shaker. Fill with ice and shake.
    Grapefruit Bourbon Sidecar In Making
  • Strain carefully into a coupe glass and garnish with an orange and a grapefruit wedge.
    Grapefruit Bourbon Sidecar Pouring
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