Smoke & Oak Mashup: Pairing Penelope With Privada!

Welcome to a brand new Whiskey Wednesday installment! Please consider this the first Smoke & Oak Brand Mashup. From time to time, I’ll be taking two to three whiskeys from one whiskey brand and two to three cigars from a cigar brand and seeing how well they pair with each other…or if they pair at all. This week’s pairings consist of three Penelope Bourbons (Penelope Bourbon, Penelope Architect, and Penelope Toasted Series) and three selections from Privada Cigar Club’s new core line (Mad Monkey, 1491, and Kings County). Let’s see how these two brands MASH up!

Penelope Bourbon
80 Proof – $35.00

Coming in at 80 proof, this is Penelope’s entry proof bourbon expression. When sipping on this alone, I get a fairly thin mouth feel. From an 80-proof bourbon, that can be expected. Slight flavors of oak and vanilla on the palate and orange peel on the finish. The finish is gone almost as soon as you drink it. When pairing this with a cigar you will need to make sure you smoke something light so it doesn’t over power this bourbon.

PCC Kings County 

Being one of the lightest of the Privada Core Line, the Kings County offers you flavors of earth, cocoa, slight white pepper, and dried fruit with a medium to short finish. When you pair these two together you don’t have to worry about them fighting for attention. The orange notes from the bourbon and the white pepper and cocoa note from the cigar adds a little more depth and dimension to the experience that they both need. I found that the finish of the cigar lasted just a little longer than the bourbon which allowed the flavors to blend and mesh well together then fade away leaving you ready for another taste. 

Notes: When trying this cigar with the other two bourbons, both overpowered the cigar so much that I couldn’t taste the cigar at all. The cigar became more like smoking warm air with little to no flavor.

Penelope Architect
104 Proof – $59.99

Stepping up to 104 proof, this Penelope expression was finished with the addition of French oak staves to add to its flavor and complexity. On the nose you get sweet notes of apple, sweet corn, and vanilla and then on the palate you are met with a youthful vanilla, dark fruit notes and a cinnamon and black pepper rye spice on the finish. This bourbon needs a good medium body cigar to match its profile.


The 1491 hits right in the middle (strength wise) of the Privada Core Line. This cigar offers notes of black pepper, nuts, and earth and a slight honey sweetness on the palate and black and white pepper and nuts on the retro. When paired with the Architect, the bourbon helps to accentuate the sweet honey notes of the cigar and brings out a slight floral note. The rye spices of the bourbon match so well with the black pepper notes on the 1491 that when experiencing these two together, the flavor notes help lift up the total profile to help create a whole new experience.  

Notes: When smoking this cigar with Penelope’s standard offering, the 1491 is definitively the star of the show. The 80-proof bourbon is so light on the palate that you can tell its there but you can really pull any one particular note from it. When smoked with the toasted expression it’s the exact opposite. All bourbon all the time. I’m not saying that’s a bad thing but, if you are wanting to experience both the cigar and the bourbon, this might not be the pick for you.

Penelope Toasted Series
115 Proof – $89.99

Penelope Barrel Strength Toasted Bourbon is 115 proof points of toasted marshmallow, chocolate and caramel goodness. The finish is soft and sweet and drinks easier than most bourbons at this proof. To me, this is sitting outside by the fire, making smores, and enjoying everything that fall has to offer kind of good! When looking for a cigar to pair with a bourbon that is this bold and is at this proof point, you want something that is more full-bodied with lots of flavor.

Mad Monkey

The Mad Monkey is possibly the strongest of the Privada Core Line. I like to call this pairing Sweet and Spicy! The Mad Monkey starts off by giving you lots of dark chocolate, earth, baking spices with a creamy smoke texture. The retro brings lots of black pepper and cedar. When you get into this cigar the smoke brings you dark chocolate and spice and when you take a sip of the bourbon its slowly transitions into a sweet chocolate and dark fruit with a hint of toasted marshmallow on the finish. When pairing them together you don’t get much of a fight for attention but a constant transition from dark and spicy to sweet and toasty. It’s a great compliment of two contrasting and bold profiles. 

Notes: When pairing this bourbon with the other two cigars, it completely overwhelms them. Its bold flavors and higher proof was a one-two knockout punch on them both.

As always, I want to thank you so much for taking the time to read this. If you’ve tried any of the Penelope Bourbons with any of the Privada Core Line, or if you’re thinking of trying, let everyone know about it in the comments below! I love good conversation and being able to hear about what you enjoyed or what you didn’t. If you’re going to enjoy a little smoke & oak, just remember, “Life’s too short, enjoy the good stuff”…. and do it responsibly!