Pappy Van Winkle cigars unite the Van Winkle family's bourbon heritage with Drew Estate's cigar-making in Estelí, Nicaragua. For the Family Reserve Barrel Fermented line, Drew Estate works directly with Pappy & Company and the Van Winkle family. Kentucky fire-cured tobacco is sent to St. James Parish, Louisiana, where it undergoes perique-style fermentation under pressure inside retired Pappy Van Winkle bourbon barrels.

That barrel-fermented leaf is combined with hand-selected Nicaraguan filler, an Indonesian binder, and a distinctive Kentucky fire-cured, barrel-fermented tapa-negra-style wrapper over an Indonesian cover leaf. Drew Estate describes the process as a three-year wait, resulting in a medium-bodied cigar marked by charred oak, peat-like smokiness, and burnt coffee. It is a true production collaboration, not merely bourbon-branded packaging.