Pappy Van Winkle Barrel Fermented Cigars


We offer cigars in 3 divine sizes: Robusto, Toro and Churchill. 10 cigars come in each lined, custom wooden box.

Rubusto Cigar

Our shortest cigar: Size 5.25 x 52
Order a Rubusto Box

Our medium-length cigar: Size 6 x 52
Order a Toro Box

Churchill Cigar

Our longest cigar: Size 7 x 48
Order a Churchill Box


While supplies last, if you order one box of each size cigar (Robusto, Toro and Churchill — 3 boxes total), you'll receive The Pappy Drew Limitada for free. For the Pappy Van Winkle and/or Drew Estate fanatic, the Pappy Drew Limitada is a commemorative vitola, consisting of three cigars. These cigars are not for sale. They're an exclusive gift from our families that are to be enjoyed during one of your most special moments — or perhaps placed away and saved as a collection piece. This free gift is available while supplies last and is limited to one per customer.

* One free gift per customer account, no matter how many boxes purchased or orders placed. While supplies last, purchase 3 boxes, one of each size cigar, and receive the Pappy Drew Limitada, a commemorative vitola consisting of three cigars, as our free gift.



Our Cigars are Back … for Good

We’re happy to announce that due to the demand of our Pappy Van Winkle Barrel Fermented Cigars, we have invested even more into our exclusive manufacturing partnership with Drew Estate. What does that mean to you? No pre-ordering, no long wait-times and no need to hide them away for special occasions. Enjoy your cigars whenever you like.

Select your choice of Pappy Cigars for spring today. They also make cherished gifts to bring and share at weddings, birth announcements, bachelor parties, golf outings and other celebrations.



Drew Estate Barn Smokers

These completely unique, annual experiences bring the cigar smoker to the barn level and teach them the ins and outs of tobacco growing, processing and finishing. This year, Pappy Van Winkle Barrel Fermented Cigars will be featured at the new Louisiana Barn Smoker in November 2017. The event will tie in the Perique tobacco and pressure-fermentation technique that is from Saint James Parish, Louisiana and is an aspect of our blend.

Explore their website for more details coming soon.



The Pappy Van Winkle Barrel Fermented cigar is a 100% long-filler, premium cigar made totally by hand in very small batches at Drew Estate in Estelí, Nicaragua.

In November 2014, we announced the partnership with Drew Estate for this new Pappy Van Winkle barrel-fermented, premium, handmade cigar. This partnership allows both bourbon fans and cigar connoisseurs to experience a flavor combination that is unique and that will remain consistent throughout each small batch.

Although it 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.

The strength level of this cigar line is “Medium Plus,” which allows both new smokers and experienced aficionados to enjoy the blend. It’s a well-rounded, sophisticated cigar with body and a hearty expression.

These cigars are sold exclusively by Pappy & Company. Each order features 10 cigars nestled in a lined, custom wooden box. Please be advised that the seal may be cut as they are randomly selected while going through customs. They are hand-rolled and shipped from the Drew Estate factory in Estelí, Nicaragua.


Drew Estate is known for passion and innovation. Making premium cigars is their “raison d’être” (reason to be). The Pappy Van Winkle Barrel Fermented Cigar is truly a showcase of their expertise.

The story of this historic bourbon-barrel-fermented cigar starts, where else, but in Kentucky, USA. It features Kentucky seed and Kentucky grown tobacco.

Once grown, the tobacco leaves — harvested and carefully selected for the blend — are cured in the traditional Kentucky style via fire curing. We then ship the leaves, used as the wrapper, from Hopkinsville, Kentucky to Saint James Parish, Louisiana. This is where the tobacco undergoes barrel fermentation.

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.

The intense pressure is what ferments this Kentucky seed. When you walk into the rooms of the barrel-fermented tobaccos, you immediately smell something very similar to the yeasty smell of a distillery. Once fermented and properly packed up, it's then shipped to the factory in Nicaragua.

Three unique sizes of these handmade premium cigars are produced at the La Gran Fabrica Drew Estate factory in Estelí, Nicaragua. A select team of Drew Estate rollers meticulously craft each cigar 100% by hand.

The Pappy Van Winkle Barrel Fermented Cigar has two wrappers: the Kentucky grown leaf blended over a Mexican San Andres leaf. Jonathan Drew, founder of Drew Estate, calls the process of blending wrappers "tapa negra."

The binder and filler of the cigar are made up of all-Nicaraguan tobaccos, personally selected by Jonathan himself.

Once complete, the cigars are packaged in custom, ten-count, lined, wood boxes and shipped back to Pappy & Company. The final blend is the perfect compliment to any bourbon and a reason in itself to celebrate.


In early 2017, our family traveled to Estelí, Nicaragua, home of La Gran Fabrica Drew Estate factory. We were invited by founder, Jonathan Drew, to their annual “Cigar Safari,” a four-day, three-night trip and factory tour. It was so much fun to meet the staff and watch our Pappy Barrel Fermented Cigars being handmade and rolled right before our eyes at their majestic factory.

Drew Estate was a gracious host, and it’s clear that its employees are true artisans. We definitely appreciate all of the work and craftsmanship that goes into each cigar.

Reflecting on our visit, we are so proud to continue this partnership. Both of our companies are dedicated to high-quality, handmade products, and this trip confirmed it for us. The finished cigar is a perfect pairing for our family’s whiskeys, and we hope you enjoy them as much as we do.