Disclosure: the sample for this review was provided at no cost. Our tasting notes and score are our own.
A little background
Penelope Cigar Sessions: Chapter 2 is a limited release American whiskey from Penelope Bourbon, created in collaboration with Alec Bradley Cigars as the second release in the brand’s annual Cigar Sessions series, following Cigar Sessions: Chapter 1. It is a blend of a 36% rye bourbon, barley malt whiskey and American light whiskey, aged six years and bottled at 117.4 proof (58.7% ABV). The combined mash bill is 69% corn, 19% rye and 12% malted barley, and the suggested retail price is $79.99. It is made in small batches and sold at select retailers nationwide while supplies last.
Chapter 2 was built specifically to pair with medium to full-bodied cigars. Penelope’s blending team and Alec Bradley’s cigar blenders worked together from the start, adjusting the blend, tasting it alongside the cigars and refining it until the proof, depth and flavor could stand up to a bolder smoke without either one overpowering the other. Penelope Bourbon was founded in 2018 by Michael Paladini and master blender Danny Polise and is named after Paladini’s daughter, while Alec Bradley takes its name from founder Alan Rubin’s sons, Alec and Bradley. This whiskey was bottled in Lawrenceburg, Indiana.
(Tasted neat from a Glencairn Glass)
Color
Dark Gold
Nose
Toasted oak, caramel, baking spice, vanilla, orange citrus, brown sugar, rye spice, and oak.
Palate
Caramel, baking spice, charred brown sugar, baking cocoa, toasted oak, sweet corn, molasses, pipe tobacco, and baking spice.
Finish
Toasted caramel, cereal grain, baking spice, black pepper, and toasted oak.
In closing
Penelope Cigar Sessions: Chapter 2 is a sweet, spice-forward American whiskey with plenty going on in the glass. The nose opens with toasted oak, caramel, vanilla and brown sugar, brightened by orange citrus, while baking spice and rye spice stand out throughout. The palate is noticeably thick and oily, moving from caramel and baking spice into charred brown sugar, baking cocoa, toasted oak, sweet corn, molasses and pipe tobacco. The finish is pleasantly long, with toasted caramel, cereal grain, baking spice, black pepper and toasted oak leaving sweet and spicy notes lingering.
Sweetness carries from start to finish, and there is enough complexity to keep each sip interesting. As with most cigar-focused releases, this whiskey is equally enjoyable with or without a cigar, so don’t feel it can only be appreciated alongside a smoke. This tasting was done neat without a cigar, and it was thoroughly enjoyable on its own. At $79.99, it is a fair price for a six-year-old whiskey at 117.4 proof with this much depth and texture, and it is an easy buy for me. Very pleasant.
NOTE: The sample used for this review was provided at no cost courtesy of Penelope Bourbon. We thank them for the sample and for allowing us to review it with no strings attached.
Penelope Cigar Sessions: Chapter 2
117.4 Proof
- Nose 8.6
- Palate 8.8
- Finish 8.9
- Complexity 8.9
- Value 8.8
Please enjoy responsibly. Never drink and drive.




