Smoke & Oak

Few pairings feel as enduring or iconic as a fine cigar and a well-aged spirit. From Southern porches and club lounges to weddings and baby showers, the combination has become a deep-rooted ritual of luxury, leisure and celebration. The earliest connection between cigars and spirits is more difficult to pinpoint. One oft- repeated, though unverified theory, attributes their first pairing to the Anglo-Spanish War in the late 1700s, when, rumor has it, the British supplied Scotch whisky and the Spaniards brought Cuban cigars.

What we do know is that by the 19th century, the cigar industry was booming across the Americas, and so were whiskey and rum. As cigar manufacturing flourished in Cuba, New York and Tampa’s Ybor City, whiskey and rum production grew across the United States and the Caribbean. In 1885, Oscar Hammerstein patented the first cigar-rolling machine, helping to seal cigars’ place in American culture.

For Jorge Luis Padrón Jr., grandson of José Orlando Padrón, who founded Padrón Cigars in 1964, a deeply personal story lies at the heart of their cigars. “I still remember my first walk through the tobacco fields in Estelí,” he says. “The soil smelled rich, almost like promise. That’s where the flavor starts. It’s where every great cigar begins. That care and attention, from field to humidor, defines the experience.”

THE ART OF THE PAIRING

Eventually, the mingling of cigars and distilled spirits became a quintessential combination. Both indulgences are crafted with layers of flavor and are meant to be savored
slowly. Pair the right cigar with the right spirit, and the flavors and experience of one enhance the other.

“It’s the same concept as pairing food with wine,” says Ashley Devlin, Bartender at River Bar & Lounge inside The Cloister at Sea Island, which offers a humidor with a wide selection of cigars and full cigar service. “Like with a steak, you’d want a nice earthy cabernet. There’s a time and a place for everything.”

“Each cigar has its own personality, but the common thread is an earthy, bold flavor,” Padrón says. “The Dámaso is mild and nuanced, the 1964 Anniversary strikes a balanced, medium-bodied note, and the Family Reserve is smooth, rich and full-bodied. You taste these layers slowly, and the right spirit can bring out something new in each one.”

Like wine and food, each cigar and spirit pairing is unique, but there are some general rules of thumb when it comes to complementary flavors. Mild-bodied cigars are lighter, sweeter options that Devlin often recommends for newer smokers and typically pair well with smooth, buttery spirits — a fat-washed bourbon, for instance — or cocktails that complement the cigar’s creaminess.

Medium-bodied cigars are typically smoother and richer with notes of cocoa and caramel. For these, Delvin will often recommend a contrast. Something with smoke or earthiness, such as a peaty Scotch, will balance out the more dessert-like notes. Full-bodied cigars offer a strong, woody intensity and “take a longer time to smoke and settle,” Devlin says. These qualities call for a high-proof or well-aged spirit that can hold its own, such as an aged rye or Cristalino tequila, which is a less traditional yet surprisingly complementary choice. “You still have that smoke and minerality plus the heaviness of an añejo tequila, but it’s often charcoal filtered. It goes perfectly with these big, heavy cigars,” Devlin explains.

REDEFINING THE RITUAL

Pairing a tequila with a heavy cigar may seem unexpected in Western cigar culture, but it reflects a larger shift in the modern cigar experience: more accessibility, personalization and. exploration. While Scotch and bourbon remain classics, more exploratory pairings, like tequila, are opening up new flavors and a new audience.

“I’ve seen more tequila drinkers having cigars, especially those who want the Clase Azul or any of our rich añejo tequilas,” Devlin says. “They could be just as great as having a Scotch.” For Padrón, the ritual itself remains unchanged. It’s about presence and slowing down. “Cigars and spirits are both long, drawn-out experiences,” he reflects. “Smoking a cigar is a process, just like sipping Scotch neat. For many, it’s a moment to unwind and not be in a rush.” His personal favorite pairing? A peaty Scotch alongside the Padrón 1926 80th Anniversary. “The flavors mix beautifully,” he says, a perfect example of tradition meeting thoughtful enjoyment.

The ritual remains, but the rules are more relaxed. “It’s becoming something more friendly to all audiences,” Devlin says. “Having a cigar and a cocktail after dinner isn’t strictly a golf-club tradition. It can be for anybody.”

While there’s no denying the classic appeal of aged spirits and bold cigars, beginning with a very mild selection, like an Acid Blondie or a Macanudo, paired with a citrusy cocktail may seem more welcoming to a curious newcomer. “It makes for a really nice nightcap,” Devlin says. “You still feel like you’re enjoying a cigar, but it doesn’t always have to be a stereotypically heavy cigar session.” It’s about the experience, “the flavors, the atmosphere and the slow enjoyment. That’s what draws people in,” Padrón adds.

ISLAND SPIRITS

River Bar & Lounge in The Cloister houses the resort’s on-site humidor, featuring a carefully curated menu organized by cigar strength, ranging from mild to full-bodied. The humidor’s extensive catalog is designed to guide both aficionados and curious newcomers on their cigar-tasting journey. Members and guests enjoy full cigar service, including assistance with selection, cutting and pairing.

“Anyone who wants to enjoy a hand-selected cigar in the moment, whether it’s with family, a partner or whatever the occasion may be, we have something for everyone,” Devlin says.

The Men’s Locker Room at The Lodge offers a dedicated fireside cigar room, perfect for those seeking a quieter, more intimate setting to enjoy a smoke and a sip. “Both cigars and spirits have layers of complexity,” Padrón remarks. “Together, they create a moment worth savoring — whether you’re celebrating, reflecting or simply enjoying the present.”