About the Fancy Free cocktail

The Fancy Free is a lesser-known but elegant bourbon cocktail that first appeared in the 1939 edition of Esquire’s Handbook for Hosts.

It’s a variation on the Old Fashioned, swapping out sugar and bitters alone for a mix that includes maraschino liqueur and two types of bitters.

Though it never reached the fame of the Old Fashioned or Manhattan, the Fancy Free has been rediscovered by modern bartenders for its balance of sweetness, spice, and subtle cherry notes.

It’s simple, spirit-forward, and true to the tradition of classic whiskey cocktails.

What Makes the Fancy Free Cocktail Special

The Fancy Free is essentially an Old Fashioned with personality. Bourbon provides the warm, caramel backbone, while maraschino liqueur adds delicate cherry sweetness and a hint of nuttiness.

A combination of Angostura and orange bitters brings balance and depth.

It’s a cocktail for whiskey lovers who want something familiar yet distinct—rich and smooth, with just enough complexity to keep you coming back for another sip.

Spirit Swaps and Food Pairings

• Swaps: Rye whiskey can be used instead of bourbon for a spicier edge.

  • Luxardo maraschino is the classic liqueur of choice, but other cherry liqueurs may be substituted if needed.

• Pairings: The Fancy Free pairs beautifully with smoked meats, charcuterie, sharp cheeses, and dark chocolate desserts.

  • It’s also excellent alongside a cigar or as an after-dinner sipper.

Closing Thoughts

The Fancy Free is a reminder of how small tweaks can elevate a classic.

By adding maraschino liqueur and a blend of bitters, it transforms the Old Fashioned’s simplicity into something richer and more nuanced—a drink that’s understated, elegant, and worth rediscovering.