Cigar Review: Pappy Van Winkle – Family Reserve Barrel Fermented

  • Cigar Reviewed: Pappy Van Winkle Family Reserve Barrel Fermented Flying Pig
  • Country of Origin: US / Nicaragua
  • Factory: Drew Estate
  • Wrapper: Kentucky Fire-Cured / Barrel Fermented Tapa Negra, Mexican San Andres Base
  • Binder: Nicaraguan
  • Filler: Nicaraguan
  • Length: 3 15/16
  • Ring Gauge: 60
  • Vitola: Double Perfecto


Back in 2014, Drew Estate partnered with Pappy & Company in order to make a small batch cigar line that Pappy & Company could sell it exclusively under the premise that it would pair with Pappy & Company’s bourbon and rye. The result is the Pappy Van Winkle Family Reserve Barrel Fermented. There are two things, aside from being a flying pig, that in theory make this a stand out cigar blend.

The first is that Drew Estate incorporates its Kentucky-grown Fire Cured tobacco into it. Usually cigars are air cured, where the tobacco is hung in a barn for a period of several weeks to dry out the leaf. The fire cured tobacco, on the other hand, is dried out by hardwoods that are kept continuously burning with low smoldering flames to dry out the leaf. The difference is usually a camp-fire like flavor in the leaf.

The second is that after the Kentucky tobacco has finished fire curing, it is put into barrels where it is actually fermented, rather than simply aged. The fermented tobacco is incorporated into the cigar as a tapa negra wrapper over a Mexican San Andres base wrapper. Because this rests on the cap of the cigar, it creates a segmented wrapper effect which is kind of neat to see.

I admit, I bought a box of the cigar on the premise alone as a huge Drew Estate fan. The box is not as impressive as I would have hoped but still pretty. The cigars on the inside are the important part though. They are adorable with their little pig tails. The caps are a rich dark espresso bean color. The rest of the little cigars are a medium brown color. To the touch, I find them to be a little oily and very smooth. The band is large compared to the cigar, with its portrait of Julius Van Winkle, the founder of Pappy Van Winkle. In gold, gothic lettering above the portrait is the “Pappy Van Winkle’s” and below the portrait it says “Family Reserve.” Aside from its off-putting size, it’s a rather iconic seeming sort of band.

The cigar smells like coffee and campfires. It lights easily but not evenly, though it straightens out later. During the first third, I pick up mocha flavors and a sweetness that speaks to the bourbon fermentation. The mocha flavors of chocolate and coffee vary in intensity but compliment the woodiness of the overall cigar.

The second third, the bourbon sweetness overcomes the mocha flavors. Now there is most definitely caramel and sugar. There is also more woodiness, like cedar. By now the cigar has evened out its burn with a minor touch up. The ash is a pretty, light grey and the smoke wafting in the air is minimal.

By the last third, some earthiness develops. I now taste the cedar as the overall flavor. There are some notes of mocha still. Not so much of the bourbon. The cigar is difficult to nub but I manage it just the same.

The burn rate was ideal and for its small size never began to burn too hotly. Overall, the cigar is a lovely little break from the day. I recommend it for mid-afternoon breaks from work, as it takes up just the right amount of time to induce relaxation before diving back into the stress of working.

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