Caramel | Green apple | Pepper | Clover honey | Pear | Lemon | Nutmeg | Toasted oak

Crème brûlée | Sweet corn | Sugar cookie | Sweet oak

Black pepper | Rye spice | Burnt caramel | Pine | Hint of smoke | Short with lingering heat

There is no legal definition of what a cigar batch whiskey has to be, but producers have generally settled on a style of multiple finished whiskeys, resulting in a big, bold, varied flavor profile. Penelope is one of the few, and certainly the largest producer, to eschew that line of thinking and set out to redefine what a “cigar batch” whiskey is.

But venturing down your own path leads you to uncharted territory full of trials and tribulations.  Penelope Cigar Sessions: Chapter 1 was a mixed bag. Part of that had to do with the new direction Penelope took with a cigar batch whiskey, bringing a lighter flavor profile into the mix. But it didn’t quite work with a cigar in terms of standing up alongside a cigar’s dominant flavor.

For Chapter 2, Penelope’s blending team worked with Alan Rubin, the man behind the premium handmade cigar brand Alec Bradley, to “create a whiskey specifically designed to complement medium to full-bodied cigars.” As with Chapter 1, the whiskey is made with a rye bourbon (presumably not with a French oak stave finish), an American single malt, and an American light whiskey. The blended components for Chapter 2 resulted in a mashbill of slightly higher corn and rye 69% corn, 19% rye, and 12% malted barley, versus Chapter 1’s 72% corn, 15% rye, 13% malted barley.

On the nose, the strong confectionery American light whiskey scents are pulled way back from last year’s edition. Chapter 2 is more bourbon-forward with its caramel, pepper, nutmeg, and toasted oak. Lighter scents of green apple, honey, pear, and lemon add just enough variation, but overall it's fairly light. The palate is the sweetest part of the sip thanks to notes of crème brûlée, sweet corn, sugar cookie, and sweet oak. Though that sounds like a sugar bomb, the sugars quickly give way to pepper and rye spice in the finish. Burnt caramel, pine, and light smoke ride out the rest of the sip, ending quickly with lingering heat.

While I miss some of Chapter 1’s more pronounced American light whiskey notes, Chapter 2 is more varied overall. The proof is thankfully up 16 points for the second outing, and it's instantly noticeable as the sip also holds up better against a cigar. Penelope perhaps held back last year’s proof to satisfy its core customer, but it came at a detriment to the overall sip.

On its own, Cigar Sessions: Chapter 2 still isn’t the sipping whiskey some want it to be. Even at a higher proof, flavors taste tempered; perhaps it's the amount of single malt and American light whiskey included, or that they are canceling each other out in a way. Penelope’s quest to buck the current cigar batch trend is worthwhile, as not everyone wants a bold whiskey to pair with a bold cigar. Contrast is needed, and it's what Penelope is striving for. It’s clear now that it is easier said than done. While it’s not enough to warrant a higher rating, Chapter 2 slightly improves on Chapter 1, but the whiskey is still trying to find its voice.