The Fancy Free is what happens when an Old Fashioned gets bored with plain sugar. The bourbon stays, the bitters stay, and the old-fashioned glass stays, but maraschino liqueur steps in as the sweetener. It sounds like a modest change, but in the glass, it makes the drink meaningfully more interesting.
Maraschino liqueur is not cherry syrup, despite what its name may suggest. It is drier, nuttier, slightly floral, and just interesting enough to keep you paying attention. Against bourbon, those flavors settle among the vanilla, caramel, and oak without covering them up. The cocktail remains unmistakably whiskey forward, but its sweetness has more texture and a little mystery.
Then come the bitters: all five dashes of them! Angostura brings dark spice and herbs, while orange bitters sharpen the edges with a cleaner citrus note. That may sound like a lot of bitters because, frankly, it is. They are doing more than seasoning the drink; they keep the maraschino in line and give the bourbon plenty of room to speak.
Serve the Fancy Free over fresh ice with an orange twist. The first sip feels comfortably close to an Old Fashioned, then the cherry, almond, spice, and citrus begin to show themselves. It is an ideal drink for when you want something familiar, but not quite predictable. The name gets it right: a little fancy, certainly, but free of any real fuss.
Check out the full recipe here:
Fancy Free
Bourbon, Maraschino Liqueur, Angostura Bitters