Small Company with a Big Heart

My mission is simple: to provide the best cigar deals and service to my customers at the lowest cigar prices possible. I take great pride in my 22 year old company, our commitment to customer service and in the products we sell. We have been in business since 1995. Our Tampa online cigar store is designed to provide you with a safe and secure environment to browse our product catalog. The folks that buy from my company are more than customers, they are relationships that have been with us for many years.

Don Gregory, serving derelicts & diplomats since 1995


No, you didn’t win the lottery and you are not an heir to old money—just an average joe who breaks even by toiling in the corporate factory. An average joe with a lot of passion and a great business idea. (How many times have you heard a happy ending to that story?) How about another wrench in the equation: no investors or moral support. You ask your father to lend you $600 to buy a computer for this great business idea and the response you get is “It will never work. Why don’t you look into finding a government job?” Does all this sound like a recipe for disaster? Probably for the average Joe—not for Don Gregory.

A passion handed down from Grandfather Ted

Twenty five years ago, Don Gregory was an International Project Manager working for IBM. He wore a Tie and Suit to work every day and shared a paper infested desk with a co-worker. He created spreadsheets and ran reports. He also smoked cigars—a passion handed down to him by his grandfather. In fact, he not only smoked cigars, he appreciated really good cigars. He was one of those joes who went out of his way to find that hidden crown jewel that nobody has ever heard about. Yes, he is a treasure hunter—and he has always been good at it. He was so good at it, that it sparked that great business idea: take the hidden treasures to the masses!

American ingenuity

With $800 in his pocket, a smattering of broken Spanish and a bunch of good-hearted Cuban connections that wanted to help the poor gringo, Don Gregory went from corporate boy during the day to The Don at night. He used his gift of tracking down obscure but incredible cigar deals and wholesaled to friends and family. When the popularity and demand for the Don’s golden finds required more than a part-time hobby, it was time to say goodbye to the office space and hello to Don Gregory’s Cigar Club & Lounge. A picturesque log cabin with rich velvet curtains, mahogany leather loungers, dazzling neon and deer head on the wall all provided the backdrop for what is now Tarpon Springs, Florida’s oldest cigar shop. The quaint little shop was born in the middle of Tampa Bay—once known as the cigar capital of the world; also the home of the most world renowned tobacco brokerage house and the most popular cigars outside of Cuba. Don Gregory had an endless wealth of buried treasure right in his backyard; just waiting to be unearthed. Sometimes “the right place at the right time” is a very profound phrase.

Don Gregory did very well during the cigar boom of the 90’s.

Cigar choices were endless as were the parties and gatherings in the Cigar Lounge. When the cigar craze lost some of its luster, the die-hard cigar smokers remained with the serious cigar shops. Real smokers, including corporate CEOs, military generals, sports superstars, retired golfers and average joes were grateful that Don Gregory was still around to offer his weekly gold coast finds. By then, the next evolution to Don Gregory’s was taking place: Don’s next great business idea.

The leather loungers were soon replaced with cigar presses, molds and pounds of loose tobacco. The Don hired a few Cuban cigar rollers with years of experience rolling in the Cuban cigar factories and started his own factory. Now, he no longer had to wander out into his back yard to find unique cigar blends; he could just have his rollers roll his own. With that, Tarpon Springs’ oldest cigar factory was born.


Don Gregory now had a 100 year old tobacco brokerage house where he could hand pick and buy the most premium tobacco before it was shipped to the islands. He had master Cuban rollers with over 20 years of rolling experience. He also had the taste to create the most exquisite cigars that rival the big name brands. The Don went to work refining his blends to offer the best for all tastes. “Mild, medium, strong and will knock you down” all describe The Don’s cigar treasures. From creamy and butter to bold and spicy, Don Gregory’s cigars have been likened to Wonder bread versus fresh bread out of the oven—out of The Don’s factory oven. When someone smokes a cigar that is so oily, it feels like they put chap stick on their lips, they understand the difference between imported cigars and The Don’s fresh, locally rolled cigars; therefore, unlike what most thought…it didn’t turn out to be a recipe for disaster.

Years and several evolutions later, Don Gregory’s is still the same private-owned, online cigar store treasure trove that offers premium quality, handrolled cigars that are all tasted and approved by the master cigar rogue himself—Don Gregory. The velvet curtains and deer head are still hanging out in the log cabin. The rollers still have their touch and Don Gregory’s passion wow’s the die-hards with every new blend he releases. It is still a place where the average joe can buy a cigar that costs less than $10 but enjoy the quality shared by the best cigars in the world. It is home to loyal customers who have found a hidden treasure and it is available to anyone who is up for a treasure hunt.