Voices From The Trail

If Enneagrams Were Bourbon Cocktails

By:Amandalin Ryan

Posted: January 14, 2026

By:Amandalin Ryan

Posted: January 14, 2026

Discover which Bourbon cocktail best represents your Enneagram personality.

What if your Enneagram type didn’t just explain your inner motivations, but also your drink order? From bold, barrel-proof classics to carefully balanced crowd-pleasers, we’ve paired each Enneagram type with a Bourbon cocktail counterpart that perfectly captures its essence. Consider this your tastiest personality test…garnish not optional.

Type 1 – The Manhattan

Classic. Balanced. Believes everything (and everyone) can be improved with a little refinement.

The Manhattan

Type 2 – The Hot Toddy

Warm, generous, and always there to help — the definition of dependable comfort.

The Hot Toddy

Type 3 – The Mint Julep

Ambitious and bold. It takes high standards to deliver results worth sipping on.

The Mint Julep

Type 4 – The Boulevardier

Complex and poetic, a little dramatic, but in the most delicious way.

The Boulevardier

Type 5 – The Whiskey Sour (& New York Sour)

Analytical and innovative, but still knows how to mix logic with a little sweetness.

The Whiskey Sour (& New York Sour)

Type 6 – The Paper Plane

Loyal, dependable, and steady even when life gets a little bittersweet.

The Paper Plane

Type 7 – The Seelbach

Life of the party. Sparkling, spontaneous, and always chasing the next great adventure.

The Seelbach

Type 8 – The Old Fashioned

Bold, assertive, and unapologetically strong. Always makes a statement.

The Old Fashioned

Type 9 – The Highball

Laid-back, harmonious, and effortlessly cool — makes everything feel a little smoother.

The Highball

Did your Enneagram match your usual order, or point you toward something new? Favorites are great, but experimenting has its perks, especially when Bourbon’s involved. Always remember to enjoy responsibly, and start planning your next Kentucky Bourbon Trail® exploration now—you might just find more than a few of these offered at our tasting rooms and partner bars.

Author: Amandalin Ryan, Director of Kentucky Bourbon Trail® Experiences

Related Articles