Skip to main content

The Manual may earn a commission when you buy through links on our site.

Treat Yourself to a Glass of Bourbon and a Pappy Van Winkle Barrel-Fermented Cigar

If you’re a fan of bourbon, whiskey, rye, and The Manual, chances are you’re already familiar with famed whiskey Pappy Van Winkle from Old Rip Van Winkle Distillery and its family of spirits. Recently, Van Winkle has added a new addition to the brand: the Pappy Van Winkle Barrel-Fermented Cigar. Much like how fish and chips are a perfect combination, so too are good cigars and bourbon (in this case, a wheated bourbon which replaced rye with wheat in its mash bill). Partnering with the Drew Estate in Nicaragua, this particular cigar is 100-percent hand-made and “allows both bourbon fans and cigar connoisseurs to experience a flavor combination that is unique and that will remain consistent throughout each small batch.”

Image used with permission by copyright holder

Before ideas of dipping cigars in bourbon begin running through your imagination, know that a barrel-fermented cigar doesn’t actually have any Pappy or booze in it at all. Here’s how the process works:

  1. First, Drew Estate takes Kentucky-grown tobacco and sends it south to Louisiana.
  2. There, the tobacco undergoes the barrel-fermentation process.
  3. Pappy Van Winkle emphasizes that “tobacco produced for premium cigars generally ferments in pilóns, a thick pile of cured tobacco stacked on boards. Instead, our alternative barrel-fermenting process uses car jacks to compress up to 500 pounds of tobacco into a 53-gallon barrel.”
  4. The high pressure then ferments the tobacco, giving off a yeasty smell very reminiscent of that of a distillery.
  5. From there, the tobacco is shipped to the Drew Estate factory in Nicaragua where it is combined with a Mexican San Andreas base wrapper. Both are wrapped around excellent Nicaraguan binder and filler tobacco.
  6. It’s then boxed up and shipped, hopefully, to you, the pleased consumer.
Recommended Videos
Pappy Van Winkle Barrel Fermented Cigar 10-Pack, Robusto – $130
Image used with permission by copyright holder

Shop Now

You can obviously opt to smoke one of these sans spirit. However, Pappy Van Winkle notes “[the cigar is] perfect for pairing with any bourbon or whiskey, Drew Estate’s favorite match is with the Van Winkle Family Reserve Rye from our family’s Old Rip Van Winkle Distillery. The spice notes from the rye bring out the pepper and smoke notes in the cigar.”

For other great cigars, check out Cigar Aficionado’s top cigars of 2018 – you won’t be disappointed.

Chase McPeak
Former Former Digital Trends Contributor, The Manual
Chase McPeak is the former Lifestyle Editor. Chase regularly appeared on Beards, Booze, and Bacon: The Manual Podcast where…
Every new Game of Thrones spinoff explained
George R.R. Martin's television world continues to grow
Matt Smith starring in House of the Dragon

When it first aired on HBO in the early 2010s, Game of Thrones dazzled audiences with revolutionary special effects and terrific acting in a unique fantasy world. Based on author George R.R. Martin's series of novels, the universe depicts the battles between several different noble families as they try to climb to the top of the continent of Westeros, both politically and figuratively. The war scenes, family drama, and massive number of characters helped make the story feel fresh and new every time a new episode aired.

As Martin's attention shifted to television and away from his books, fans have looked to the TV series to finish some of the stories he couldn't finish on the page. Game of Thrones left fans wanting more, despite its poorly received finale, and a plethora of spinoffs are on the way. House of the Dragon already has two seasons completed, and there are several others in the coming years to look forward to.
House of the Dragon
House of the Dragon finished its second season in 2024. The show chronicles the heated family dynamics of the Targaryen empire almost two centuries before the events of Game of Thrones. The third season should pick up the civil war between Queen Rhaenyra's forces and King Aegon's after a slow-building conflict throughout the second act.

Read more
The ultimate guide to cigar terminology: Speak like a true aficionado
The ‘I definitely know my cigars’ cheat sheet. You're welcome.
Man wearing top hat lighting a cigar in a bar

You're not the only one who has felt out of your league talking cigars with someone who obviously knows his stuff, trust me. To everyone else, the cigar world is a secret society with its own language—a mix of tradition, craftsmanship, and ritual that may as well be code to the onlooker. But here’s the secret–you don’t need years of puffing to sound like an aficionado.

This guide explains cigar jargon in the most approachable way possible. No BS, no elitism, no jargon— just straight talk in plain, everyday words. You’ll learn the basic structure of cigars, how to describe what you’re tasting, and how to talk shop without sounding like a rookie. Whether you’re sparking up at a lounge, perusing a humidor, or just kicking back, having the lingo effortlessly rolling off your tongue will elevate your cigar game instantly.

Read more
No more pay-per-view? UFC signs exclusive streaming deal with Paramount
The deal will start in 2026 and run through 2032.
The UFC Championship belt.

Under a new deal announced on Monday, Paramount will become the exclusive streaming home for UFC events for the next seven years in the US. The deal, which Paramount reached with TKO Group, has an average annual value of $1.1 billion, according to the companies.

Under the terms of the deal, Paramount will stream UFC's full slate of its 13 marquee numbered events and 30 "Fight Nights" on its streaming platform, Paramount+, with some events also being simulcast on CBS, starting in 2026.

Read more