Penelope Cigar Sessions Chapter 01: A Bourbon Built for Smoke & Stories
Some bottles appear by chance, waiting quietly on a shelf for you to stumble across them. Others you hunt down — driven by curiosity, reputation, or just a name that dares you to find out. Penelope Cigar Sessions Chapter 01 falls squarely into that second category.
Anytime you put the word cigar on a bourbon label, expectations instantly skyrocket. Will it be bold enough to stand up to a Maduro? Will it lean too sweet and fade into the smoke? Or will it strike that rare balance — a pour that complements a cigar without needing one?
That’s exactly what we set out to discover in this week’s Tortured Bourbon Monday Episode.
👉 Watch the full episode here:
The Basics: What’s in the Bottle?
Proof: 101
MSRP: $80
Age: 6 years
Mash Bill: 72% Corn | 15% Rye | 13% Malted Barley
Company: Penelope Bourbon
Finish: French oak staves
Penelope has carved out a reputation for creative finishing projects — from the Architect series with French oak, to Rio with honey and amburana, to the elusive Cigar Blend that sells for triple digits (if you can even catch one in the wild). With Cigar Sessions, they’ve given us something more grounded: a fair price, elegant oak influence, and a proof point that doesn’t overwhelm but still delivers plenty of character.
The Nose: Dessert Meets the Humidor
First whiff, and I couldn’t help but grin. This bourbon isn’t shy. The nose leaps out with milk chocolate, vanilla, and candied apple. Imagine strolling past a caramel apple stand at the fair while holding a chocolate bar — that’s the vibe. Sweet, inviting, but also layered enough to keep you lingering.
The Palate: Layered & Balanced
On the sip, Penelope Cigar Sessions adds a twist: chocolate and dried peach. That fruit note keeps things lively, lifting the darker sweetness. Mid-palate, the profile settles into the cigar lounge zone: tobacco and warm caramel.
It’s like sinking into a leather chair, cigar in hand, with a plate of chocolate-covered dried fruit within reach. This isn’t a powerhouse pour — it’s not trying to knock you out. Instead, it’s measured, intentional, and smooth enough to enjoy whether you’re pairing it with smoke or not.
The Finish: Toffee & Dark Fruit Glow
The finish finds that Goldilocks spot — not short, not overly drawn-out. Toffee, dark fruit, and light oak linger in harmony. No harsh tannins, no bitter edges. Just a warm, balanced close. If the nose was a carnival and the palate was a cigar lounge, the finish feels like the quiet walk home — calm, steady, memorable.
Where Does It Rank?
In our Tortured Bourbon Monday Episode, Heather and I debated what makes this bottle stand out and where it lands in our rankings. Spoiler: Penelope keeps proving they can punch above their weight.
At $80, this isn’t a once-a-year splurge — it’s a bottle that feels premium without draining your wallet. And when you stack it up against other “cigar bourbons” on the market at $200+, this feels like a steal.
Final Thoughts
Penelope Cigar Sessions Chapter 01 delivers exactly what it promises: a bourbon built to shine alongside a cigar, but more than capable of standing on its own. With chocolate, tobacco, caramel, and toffee woven through each sip, it’s indulgent and complex without ever going over the top.
If you’re a Penelope fan, it’s an easy buy. If you’re a cigar lover, it’s a must-try. And if you’ve ever wondered whether a bourbon can truly be designed to pair with smoke — this bottle makes the case.
Sip what you like. Share what you love. Don’t get tortured chasing bottles that don’t fit your palate.
Cheers, y’all. 🥃🔥
