How Jorge Luis Valdes and Aquiles Legra turned a home-based cigar business into a South Florida institution—and helped shape Miami’s modern cigar culture.
By MiamiBusiness.com
There was a time in Miami when smoking a cigar meant something very different.
Before cigar lounges became gathering places for entrepreneurs, executives and celebrities, before premium cigars became intertwined with fine spirits and nightlife, and before Miami’s cigar culture became part of the city’s identity, cigars were often associated with another generation.
Then came the cigar boom of the mid-1990s.
Suddenly, cigars were everywhere.
Hollywood stars appeared on magazine covers holding them. Businesspeople gathered over them. Premium cigar brands became objects of fascination. A younger generation began learning about wrappers, fillers, countries of origin and the craftsmanship behind a properly made cigar.
Miami, with its Cuban heritage and natural connection to tobacco culture, was perfectly positioned for the moment.
And right in the middle of that transformation were two men whose very different paths would eventually converge: Jorge Luis Valdes and Aquiles Legra.
Today, they are the 50/50 partners behind Sabor Havana Cigars, a South Florida cigar institution whose story began more than three decades ago—not with a sophisticated lounge or a major retail operation, but with an airline employee looking for a different future.
Before Sabor Havana
In the early 1990s, Jorge Luis Valdes was working for Northwest Airlines.
It was a good corporate job, but around 1992 circumstances began to change. When the airline reduced his salary, Jorge started thinking seriously about creating another source of income.
That setback would ultimately provide the motivation for what came next.
Jorge was already developing relationships within the cigar industry and would become a broker representing major premium cigar brands. He saw an opportunity developing around cigars and began considering a business of his own.
One of the most consequential conversations happened in a place about as far removed from an elegant cigar lounge as imaginable.
A Denny’s on Bird Road.
Jorge sat down with his friend Juan Mesa, and the two began brainstorming.
They needed a name.
Something Cuban without being inaccessible. Something that worked in Spanish but could also be understood by an English-speaking customer.
They arrived at two words:
Sabor Havana.
The flavor of Havana.
In 1994, Jorge Luis Valdes launched Sabor Havana Cigars, initially operating it as a mail-order cigar business from his home.
There was no elaborate lounge.
No cocktail program.
No sprawling event.
Just an entrepreneur, cigars, customers and an idea.
When Northwest Airlines subsequently offered Jorge an early-retirement package, he took it.
The airline chapter was ending.
The cigar chapter was just beginning.
Miami’s Cigar Boom
Across town, another future cigar entrepreneur was still living a very different life.
Aquiles Legra was working for Campbell Soup Company.
He wasn’t yet a cigar retailer. In fact, his introduction to the cigar lifestyle came through his friend Henry Vilar, who encouraged him to start smoking premium cigars around 1996.
The timing was extraordinary.
By 1995 and 1996, the American cigar boom was in full swing.
Cigar Aficionado had helped bring premium cigars into popular culture. Movie stars, entertainers, athletes and business leaders appeared with cigars. Ratings and reviews gave consumers a new vocabulary for understanding what they were smoking.
For people like Aquiles, cigars were becoming something more than tobacco.
They were an experience.
Miami embraced the movement particularly well.
The city already possessed generations of Cuban cigar history, but this was different. Premium cigars were becoming part of the contemporary Miami lifestyle.
Younger professionals were smoking them. Business relationships developed around them. Cigar stores became gathering places.
Aquiles loved the culture surrounding it.
And he began seeing the business opportunity.
Henry Vilar and Macabi Cigars
Henry Vilar would play an important role in Aquiles’ journey.
Aquiles became involved with Macabi Cigars around 1996, and in 1997, when Vilar opened another Macabi location near The Falls area, he asked Aquiles to join him.
The man who had introduced Aquiles to cigar smoking was now introducing him to cigar entrepreneurship.
Aquiles immersed himself in the business.
He learned the products, the manufacturers and, perhaps most importantly, the customers.
Because a successful cigar shop isn’t simply about what’s inside the humidor.
It’s about who is sitting outside it.
Customers stay. They talk. They bring friends. They discuss business, sports, politics, family and life. The relationship between retailer and customer can last decades.
Aquiles understood that.
And somewhere along the way, another cigar professional began walking through the doors.
His name was Jorge Luis Valdes.
When Jorge Met Aquiles
By this point, Jorge wasn’t simply operating his Sabor Havana mail-order business. His work as a cigar broker representing major brands took him into cigar shops throughout the market.
One of those accounts was Macabi.
That’s where Jorge and Aquiles got to know one another.
The relationship developed naturally.
Both understood cigars, but more importantly, both understood people.
By 1998, their business paths were becoming increasingly intertwined through the Macabi operation on Sunset.
Then, in 1999, they made the decision that would define the next quarter-century of their lives.
Jorge Luis Valdes and Aquiles Legra became 50/50 partners.
Sabor Havana Cigars would become their business together.
Sunset: The First Sabor Havana
The Sunset Drive store became the first Sabor Havana retail location and the foundation for everything that followed.
What Jorge had started from his home five years earlier now had a physical home of its own.
But the philosophy went beyond selling cigars.
The store became a gathering place.
Customers came to buy a cigar but often stayed for the conversation.
Friendships formed. Business relationships developed. Regular customers became part of the extended Sabor Havana family.
That atmosphere would ultimately become one of the company’s most valuable assets.
Cigars were the product.
Relationships were the business.
Building Sabor Havana
As the customer base grew, so did the company.
After Sunset came Doral, placing Sabor Havana inside one of Miami-Dade’s rapidly developing business communities.
In 2003, the partners expanded into Palm Beach, extending the Sabor Havana name beyond Miami-Dade.
They also acquired King’s Treasure / Bill’s Pipe & Tobacco, one of the area’s oldest cigar and pipe stores.
The acquisition represented something larger than another location.
Cigar shops are repositories of history. Generations of customers pass through them, and many of the old tobacconists that once served their communities have disappeared.
Taking over an established institution gave Jorge and Aquiles an opportunity to preserve part of South Florida’s tobacco heritage while introducing it to another generation.
Then came Coral Gables.
The Coral Gables Years
In 2005, Sabor Havana opened in Coral Gables.
It was a natural market.
Professionals, attorneys, bankers, executives, entrepreneurs and longtime cigar enthusiasts provided precisely the kind of clientele around which Sabor Havana had built its reputation.
But even successful businesses sometimes encounter circumstances they cannot control.
The building was eventually sold.
The new ownership increased the rent to approximately three times its previous level.
The numbers simply stopped making sense.
In 2011, Sabor Havana closed its Coral Gables location.
It was a reminder of something every longtime entrepreneur eventually learns: longevity doesn’t come from refusing to change.
It comes from knowing when to change.
The Spade
There is another piece of Sabor Havana history that customers may recognize without knowing its story.
The spade.
Jorge developed the symbol because its shape reminded him of a tobacco leaf.
But there was another connection.
Jorge owned a black Corvette, and the spade motif fit naturally with the car and its personalized license plate:
BLACKJACK1.
Cars, cigars and entrepreneurship became pieces of the same personality.
Years later, Jorge’s license plate would carry a different message.
SMOKE THIS.
For anyone familiar with Sabor Havana, the phrase needs little explanation.
From Retail to Experience
The premium cigar business has changed considerably since Jorge started mailing cigars from his house in 1994.
Consumers can purchase cigars online. Information about virtually every cigar in the world is available instantly. Ratings, reviews and videos are everywhere.
That means the modern cigar retailer has to provide something the internet cannot.
Experience.
Jorge and Aquiles recognized that long ago.
Sabor Havana developed dinners, tastings, domino tournaments, educational programs and gatherings that transformed customers into a community.
The culmination of that philosophy is SMOKETHIS®, Sabor Havana’s signature annual celebration.
It isn’t simply a cigar sale.
Manufacturers, cigar personalities, customers and enthusiasts gather to smoke, learn, eat, drink and celebrate the culture that has surrounded Sabor Havana for decades.
In many ways, SMOKETHIS® represents the evolution of the original Sunset store on a much larger scale.
People come for cigars.
They stay for the experience.
Aquiles Looks Toward Spirits
Ask Aquiles about the future and his vision increasingly extends beyond the humidor.
He sees a natural connection between premium cigars and premium spirits.
Sabor Havana has expanded the Doral operation with a cocktail lounge, creating an environment where the cigar experience can be paired with thoughtfully prepared drinks and hospitality.
The company has also moved into liquor retail through Sabor Havana Liquor Express.
For Aquiles, this isn’t abandoning the company’s roots.
It’s extending them.
The same customer who appreciates the craftsmanship behind a premium cigar often appreciates the craftsmanship behind a quality rum, bourbon, Scotch or cocktail.
The cigar remains at the center.
The experience around it becomes richer.
Jorge Looks Toward Education
Jorge’s vision for the future centers heavily on something else:
education and interaction.
Today’s cigar consumer wants to understand what he or she is smoking.
Where was the tobacco grown?
Why does a particular wrapper change the flavor?
How does aging affect a cigar?
What distinguishes one region from another?
How should a cigar be paired with a spirit?
Interactive events allow manufacturers, retailers and consumers to have those conversations directly.
For Jorge, that human connection represents something technology cannot replace.
A cigar may take an hour to smoke.
That hour creates time.
Time to talk.
Time to listen.
Time to learn.
And sometimes, time to create the relationship that leads to the next business idea.
Three Decades Later
It is difficult to look at Sabor Havana today without appreciating how unlikely the journey was.
One partner was working for an airline.
The other was working for Campbell Soup.
One started selling cigars through the mail from his house.
The other started smoking cigars because a friend encouraged him to try them.
Their paths crossed inside someone else’s cigar store.
And in 1999, they decided to become partners.
More than a quarter-century later, Jorge Luis Valdes and Aquiles Legra remain 50/50 partners.
Businesses survive economic cycles, rent increases, changing neighborhoods, shifting consumer habits and new competitors only when the people behind them continue adapting.
Sabor Havana has done precisely that.
Mail order became retail.
Retail became lounges.
Lounges became events.
Cigars expanded into spirits.
And customers became community.
The Flavor of Havana, Made in Miami
Perhaps Juan Mesa and Jorge Luis Valdes understood more than they realized during that conversation at Denny’s on Bird Road more than three decades ago.
They were searching for a name that worked in two languages.
They found one that ultimately described an entire experience.
Sabor Havana.
The flavor of Havana.
But the company that grew around those words is unmistakably Miami.
It carries the city’s Cuban heritage, its entrepreneurial energy, its appreciation for hospitality and its tendency to turn business relationships into friendships.
Jorge Luis Valdes and Aquiles Legra didn’t invent Miami’s cigar culture.
They became part of its story.
And more than three decades after the first Sabor Havana cigars left Jorge’s home through the mail, they’re still writing the next chapter.

About Sabor Havana Cigars
Sabor Havana Cigars was founded by Jorge Luis Valdes in 1994 as a home-based mail-order premium cigar business. Jorge Luis Valdes and Aquiles Legra became 50/50 partners in 1999 and developed Sabor Havana into a South Florida premium cigar retailer, lounge and events business. Today, the company continues to bring together premium cigars, spirits, education and community through its retail operations, cocktail lounge and signature events including SMOKETHIS®.
Learn more about Sabor Havana and upcoming SMOKETHIS®, events at Sabor Havana Events.

Experience Sabor Havana
Discover the premium cigars, fine spirits, events and camaraderie that have made Sabor Havana Cigars part of South Florida’s cigar culture for more than three decades. Whether you’re a longtime aficionado or discovering premium cigars for the first time, Jorge Luis Valdes and Aquiles Legra invite you to experience Sabor Havana.
Jorge Luis Valdes
Call: 786-295-3953
Email: jorgelv@bellsouth.net
Aquiles Legra
Call: 305-733-2984
Email: alegra84@aol.com
For upcoming events and information about SMOKETHIS®, visit SaborHavanaEvents.com.