The Fennel Bailey Cocktail

Gerald and Sara Murphy were rich ex-pat Americas living la Vie de Bohème in 1920s Paris. They threw fabulous parties for their artist and writer friends – F. Scott Fitzgerald, Ernest Hemingway, Pablo Picasso, Cole Porter and other luminaries – who lined up to enjoy the expertly mixed (and fully hosted) drinks developed by Gerald.

The Bailey is the most remembered of Gerald’s alcoholic inventions. In its original incarnation The Bailey calls for gin, lime, grapefruit and hand-torn mint. It’s something like a gimlet-mojito hybrid.

In this variation, the mint and lime are dropped for pure grapefruit pucker and the herbal, licorice-kick of a fennel infused simple syrup. I’m not sure Gerald would approve, but I’m quite sure Ernest Hemingway would quaff one of two with me.

Fennel Gin Cocktail


  • Superfine sugar, for coating rim of cocktail glass (optional)
  • 2 oz. Hendrick’s Gin
  • 1 oz. freshly squeezed grapefruit juice (or an equal mix of lime and grapefruit if you prefer.)
  • 2 tsp. Fennel Simple Syrup (recipe follows)

Fennel Gin Cocktail


If desired, run a wedge of grapefruit around the rim of a chilled cocktail glass. Turn the glass upside-down and dip the rim of the glass into superfine sugar. Shake off any excess sugar and set glass aside.

Shake the remaining ingredients hard with crushed ice and strain into the prepared cocktail glass.

Tip: If you don’t have a Boston Strainer, a standard cocktail trainer fits perfectly over a wide mouth Mason jar.

Fennel Gin Cocktail

For The Fennel Simple Syrup

Like most simple syrups we make, this is a 2:1, meaning 2 parts sugar to 1 part water. Scale as you need.

Bring 1/2 cup organic sugar, 1/4 cup water and one tablespoon fennel seeds to a simmer in a very small saucepan. Stir until all the sugar is dissolved. Turn off the heat and let the fennel steep for 30 minutes.

Strain the fennel seeds from the simple syrup, transfer the simple syrup to a small mason jar or other container, and refrigerate until chilled. Can be made ahead of time. Keeps for months in the fridge.


Happy weekend! Cheers!

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  1. Sarah says

    Thanks for the recipe! It inspired an awesome cocktail from what I had on hand, namely a bottle of home fennel infused vodka. I often infuse vodka or gin with random things from the garden, sometimes the infusion is a hit, sometimes it’s not, but I almost never throw the failures out, because often they do improve with age. The fennel vodka we made was way to strong and I couldn’t figure out what to do with it until I saw this post. I’d say I followed your recipe except instead of the fennel syrup I used our vodka (just a splash) and plain simple syrup and a squeeze of lime, no sugared rim. Awesome! I may even make more fennel vodka this summer.

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