To mark the occasion, I opened a bottle of Woodford Reserve Double Double Oaked Bourbon that I recently picked up. I’m a longtime fan of the standard Woodford Reserve Double Oaked, and this special expression takes an already excellent bourbon to another level. After the regular Double Oaked bourbon has fully matured, it spends an additional year in a second heavily toasted, lightly charred new oak barrel, creating a whiskey with remarkable depth and richness. Once available only as an annual distillery-exclusive release, this special bourbon now enjoys limited national distribution.

The bourbon’s deep, maple-syrup color immediately reflects the influence of that extended oak aging. Rich aromas of maple syrup and caramel rise from the Glencairn glass, while notes of butterscotch emerge as it opens up. The dark, inviting profile continues on the palate. Waves of caramel and maple lead the way, followed by hints of dark cherry and gentle spice. Taken as a whole, Woodford Reserve Double Double Oaked is dessert in a glass.

After savoring the bourbon for a while, I lit a Rocky Patel DBS. The 5 x 50 Robusto features dual Nicaraguan and Pennsylvania Broadleaf binders along with dual Honduran and Nicaraguan Broadleaf fillers. “DBS” stands for “Double Broadleaf Selection,” an appropriate name for a blend built around broadleaf tobaccos. Completing the package is a Mexican San Andrés Maduro wrapper.

The DBS opens with black pepper layered over bold cocoa and nut flavors, supported by subtle wood and vanilla sweetness. This cigar had been resting in my humidor for nearly a year, and while it remained full-bodied, it seemed slightly less intense than earlier examples I smoked closer to release. One characteristic that remained unchanged, however, was the draw. Although the cigar never appeared overly packed, every DBS I’ve smoked has drawn like a thick milkshake through a straw until about the first third, when airflow finally begins to improve. Draw issues aside, it remains a cigar I consistently enjoy.

The Woodford Reserve Double Double Oaked and Rocky Patel DBS proved to be fitting companions. From the start, the bourbon’s caramel and maple notes complemented the cigar’s vanilla and wood flavors. As the pairing progressed, espresso, cocoa, and dark fruit characteristics from both began to intertwine, creating seamless transitions across the palate. Near the finish, the cigar seemed to coax additional pepper and baking spice from the bourbon, adding another layer of complexity.

The evening of slow sipping and leisurely smoking provided plenty of time for reflection. It has taken a while, but it feels as though we’ve finally found our rhythm in retirement. The freedom to set our own schedule, whether for travel, social gatherings, household projects, or simply relaxing, is a reward earned through decades of work.

Perhaps the best indication that retirement suits me is that it took two days to find the time to sit down and write these thoughts. Boredom, it seems, is not a problem.

While Colleen prepared a selection of snacks, I mixed up a couple of Aperol Spritzes. A trip to the humidor yielded a Crowned Heads Blood Medicine Limited Edition 2026 B Positive Toro to complete the afternoon’s indulgences.

Our table was decorated with floral arrangements brought home from Friday evening’s reunion gathering. A visiting Swallowtail butterfly seemed to enjoy the flowers as much as we did, adding another touch to the bright spring ambiance.