Pensacola is about to join the ranks of Houston, Miami, Tampa, and Charlotte with its very own cigar weekend—and the woman behind it never even smoked before 2023.
Dr. Charletha Powell, the driving force behind the inaugural Pensacola Cigar Weekend (May 1–3), sat down with me on We Don’t Color on the Dog to share how a chance encounter at a convention turned into a city-wide celebration of culture, connection, and community.
From Skeptic to Organizer
Dr. Powell’s entry into cigar culture wasn’t exactly a natural fit. “I had never smoked anything in my entire life,” she admitted. “Nothing, not even in college.” It was a conversation at a convention—and a nudge from a lounge owner in Jacksonville, South Carolina—that changed everything.
She initially pictured the stereotypical cigar scene: mahogany walls, oversized ring gauges, velvet couches. “I was like, it is not for me,” she laughed. But once she tried it, she was hooked—not necessarily on the smoke itself, but on the entire world surrounding it.
“It’s such an intricate, beautiful process from seed to smoke. I might even smoke every month, but I love what it represents.”
Bringing the Culture Home
After attending cigar weekends in larger cities, Dr. Powell noticed something missing closer to home. Pensacola has two well-regarded cigar lounges—Cigar Factory and Cordova Cigars—but the community pulse was harder to find. She decided to create it herself.
“What I found with these weekends is it brings people together that would not normally be together,” she said. Vendors and cigar brands are traveling from Virginia, Maryland, Texas, Charlotte, and Houston to participate. “Little Pensacola,” as she put it, is drawing a crowd.
Three Days of Events
The weekend kicks off Friday at Cigar Factory with a VIP gathering, moves to Blend Lounge for a DJ set, then closes out the night at Cordova Cigars for an after-party. Saturday is the main event—held outdoors at Museum Plaza with a Kentucky Derby theme, perfectly timed to the race itself. Attendees are encouraged to dress the part: seersuckers, big hats, fedoras, and flowing dresses.
“Cigars, mint juleps, perfect pairing, perfect day.”
Rock Hill Cigars is sponsoring the VIP lounge, and Stars Band Live will perform alongside a DJ. Sunday wraps things up with a farewell mixer back at Cordova Cigars.
An Event for Everyone
One of the most important points Dr. Powell made? You don’t have to be a cigar smoker to attend. “The event is outside, and so we have a lot of people that are married to spouses that don’t smoke at all,” she said. “The outdoor event makes it very easy for anyone to come whether you’ve never smoked or whether you smoke every day.”
Get Your Tickets
Available at pensacolacigarweekend.com and Eventbrite.
VIP includes open bar & food · General Admission covers Blend Lounge & Saturday’s main event.
Use code LUXE10 for $10 off general admission.
Buy Tickets
