On any given evening inside Cordova Cigars, the scene unfolds slowly.
Someone is leaning back in a leather chair, letting the final light of the day filter through the windows. A few regulars are gathered around a table, debating sports or telling stories from the week. A cigar glows softly at the end of someone’s hand while the room hums with relaxed conversation.
Nothing here feels rushed.
That, in many ways, is the entire point.
For the past decade, James Overbay has been part of that environment. Until recently, he served as the shop’s general manager. Now, after years of learning the rhythms of the lounge and the community that surrounds it, he and his wife have officially taken ownership of Cordova Cigars.
The transition feels less like a takeover and more like the natural passing of a torch.
“I was given autonomy as a GM to do what I thought was best to help grow the business,” James explained. “That made the transition easy because I kind of made it my own over those years.”
But to understand where the shop is headed, it helps to understand where it came from.
From Guitar Center to Cigar Lounge
Before entering the cigar industry, James spent more than a decade working in music retail.
“I was with Guitar Center for about eleven years,” he said, describing a career that took him from Knoxville to Chattanooga and eventually to Pensacola.
The move south came after his wife accepted a job in the medical field. The couple considered several cities before deciding Pensacola felt most like home.
“We both loved the beach, and Pensacola had a feel that reminded us of where we were from,” he said.
At first, cigars were simply a hobby. James began smoking them casually in the early 2000s, often during rounds of golf with friends. Like many hobbies, curiosity led him deeper.
“I started trying to figure out why I liked some cigars and hated others,” he said. “What country does the tobacco come from. What farm? What region?”
The deeper he dug, the more fascinated he became. Soon he was watching videos, researching tobacco farms, and visiting local cigar shops where knowledgeable tobacconists helped guide him through the nuances of flavor, construction, and blending.
“They weren’t just saying ‘try this.’ They explained why you might like it,” he said.
That approach left a lasting impression. Education, he realized, was the key to helping people appreciate cigars.
Finding a Home at Cordova
Ironically, James did not originally intend to work at Cordova Cigars.
After leaving Guitar Center, he briefly pursued real estate. Looking for a place to meet clients, he began spending more time at the lounge.
“I thought it would be a good office,” he said. “You meet a lot of people.”
Eventually, he told the manager that if a part-time position ever opened, he would be interested. A call came shortly after. Within weeks, he was working behind the counter. What began as a side job quickly became something much more meaningful.
“I fell in love with the community of people here,” he said.
The shop’s regulars were unlike anything he had experienced in retail before.
“They’re family,” he said. “This is a unique environment with unique people.”
According to James, about thirty regulars form the core group that visits the lounge nearly every day. Beyond that inner circle, a much larger group of customers rotates through the shop throughout the week.
“The regulars built this business,” he said.
And that community is the heartbeat of the shop.
Teaching the Next Generation of Smokers
For James, selling cigars has never really been the job. Teaching people about them is.
One of the things he noticed early in his own journey into cigars was how much of the hobby was hidden behind unspoken traditions. New smokers often walk into a lounge without knowing how to cut a cigar properly, how to light it, or how slowly it should be enjoyed. Without guidance, many people end up having a harsh first experience and decide cigars simply are not for them. In reality, the problem is usually not the cigar. It is the process.
“A lot of great cigars are ruined by the lack of education to the end consumer,” James explained.
Lighting a cigar, for example, is meant to be gentle and deliberate. The foot of the cigar should be toasted slowly before drawing smoke, allowing the tobacco to heat evenly and produce a smooth flavor. Many beginners skip that step entirely, aggressively pulling on the cigar while trying to get it lit, which overwhelms the palate and creates a bitter first impression.
“It’s about slowing down,” James said of the ritual.
That philosophy shapes how he approaches the shop.
Instead of expecting customers to already know the rules of the cigar world, he prefers to walk them through it. Conversations often begin with simple questions: What flavors do you like? What have you tried before? Are you looking for something light, something bold, or something in between?
From there, he can guide them toward cigars that match their preferences while explaining what makes each one different. Much of that knowledge comes from years of personal study and experience. James has smoked and evaluated countless cigars, learning the subtle differences between tobaccos grown in Nicaragua, the Dominican Republic, and Honduras.
It is the same approach he used earlier in his career, selling guitars. Instead of simply handing someone an instrument, he wanted them to understand what made it special.
The goal at Cordova Cigars is the same. Education lowers the barrier to entry. It removes the intimidation that sometimes surrounds cigar culture and replaces it with curiosity. James believes that welcoming new smokers and giving them the tools to enjoy the hobby correctly is essential to the future of the industry.
After all, every seasoned cigar enthusiast was once a beginner sitting in a lounge chair, learning how to light their first cigar.
At Cordova Cigars, that learning process is part of the experience.
The Wide World of Cigars
To the uninitiated, cigars might seem like a narrow niche. In reality, the industry spans countries, climates, and centuries of agricultural tradition.
Tobacco used in premium cigars is primarily grown in places such as Nicaragua, the Dominican Republic, and Honduras. Each region produces leaves with distinct characteristics based on soil composition, climate, and growing practices.
James often describes cigars in three simple visual categories: light, medium, and dark. But the flavor possibilities go much deeper.
“There’s an enormous range,” he explained, comparing the variety of cigars to a broad palette of tastes.
Some blends are mild and creamy. Others carry notes of pepper, chocolate, leather, or coffee. Much of the blending process considers not only flavor but aroma, since the smell of a cigar contributes significantly to the overall experience.
In recent years, interest in cigars has been quietly growing again. Part of that resurgence comes from younger enthusiasts discovering the culture through travel or social media. Another factor is the desire for slower social spaces in an increasingly fast digital world.
A cigar lounge offers something rare today. Conversation without phones. Time without pressure. Community without pretense.
Building an Inclusive Lounge
One of James’s goals as the new owner is to expand who feels welcome in the cigar world. Traditionally, cigar lounges have been dominated by men. That dynamic is slowly changing, and James believes the industry must actively encourage that shift.
“It’s vitally important for this industry to welcome female cigar enthusiasts,” he said. “This is their lounge too.”
He hopes Cordova Cigars can become a space where newcomers of any background feel comfortable asking questions and learning the craft. Education, again, is the key. Many of the barriers surrounding cigars are simply the result of unfamiliar traditions that no one explains. By removing that intimidation, James believes the culture can continue to grow.
The Atmosphere of Cordova Cigars
Walking into Cordova Cigars feels different from many modern retail spaces. There are televisions showing sports. Conversations stretch across couches and chairs. Some guests stay for an hour. Others spend entire evenings relaxing with friends. James compares the shop’s customer base to the rings of Saturn.
At the center sits a small group of regulars. Around them are dozens of frequent visitors. Beyond that is an even larger orbit of occasional guests. Together, they form the ecosystem that keeps the lounge alive. It is a place where musicians, professionals, veterans, and retirees might all sit at the same table sharing stories. And often, the conversation matters more than the cigars themselves.
A New Chapter
For James Overbay, purchasing Cordova Cigars was not a sudden decision. It was the result of years of quiet planning. From early in his time working at the shop, he had already begun discussing the possibility of taking over the business one day.
“I told the previous owner that when he was ready to step away, I wanted the opportunity to carry the torch,” he said.
Now that the opportunity has arrived. There are renovations he wants to tackle. Small improvements around the shop. Fresh paint, upgrades, and long-term plans for the space. But the most important thing will remain unchanged.
The community.
Because in the end, Cordova Cigars was never just about tobacco.
It was always about the people sitting around the table.
