Celebrating Cuarenta Años with Rodriguez Cigars – Key West

The old saying that time flies is certainly true for the Rodriguez Cigar Factory in Key West, Florida. Founded in 1984 by Angel and Daniela Rodriguez, its roots go back to the family’s plantation in Las Villas, Cuba in 1947. Fleeing the tyranny of the Castro regime in 1971, Angel and Daniela eventually set up shop in Key West in 1984. Today it is the oldest operational factory on the small island.

I have been to visiting Key West for decades and every trip I make puts me at the Rodriguez Cigar Factory. It is really the only legit cigar shop on the island. I remember back in the late 1980’s, on my first trip to the island, I visited numerous shops, most of which do not even exist today. That first time I stepped into the small shop, next to the Kino Sandle Factory, I knew this was the place. So, every time my family and I would visit each year, they went shopping at the Kino factory and I would hang out at Rodriguez Cigars. Back then you would see Angel and Daniela rolling cigars, something you did not see in run of the mill shops. In fact, Daniela would make my favorites, the Rodriguez Cigars lancero. That was her specialty. I would pick up a bundle and enjoy them all week.

Time and decades slipped by and sadly Angel and Daniella past away, but their grandson Danny DiFabio picked up the reins and kept the operation running, expanding the shop to include a small sitting area, adding an aging room on the second floor, and even offering a tour to learn about cigar making and the history of cigars in Key West. He also teamed up with Guillermo Pena in Nicaragua to produce their name sake cigars.

Danny and his beautiful wife Pilar have been my friends ever since I met him over a decade ago and I was honored to be invited to his 40th anniversary celebration of Rodriguez Cigars in Key West. Thanks to Danny, I was able to get a room at the Hilton Doubletree Resort for a special family discount and I learned that I could fly round trip to Key West from Orlando for only $150.00. Ok, that means I may visit some more, it beats driving 7 hours. If you have not figured out by now, I truly love hanging out in Key West.


The Pre-Event

Once I arrived on Thursday, the 12th of December, I got settled in my hotel after a short but delayed flight. I got there in enough time to head over to the pre-event at a cool bar known as Flama Cabana located in the Havana Cabana Resort. I met some of the friends and family that would be attending the main event. The event was chill with some finely crafted cocktails including something new called the Smokey Rum Old Fashioned. It is a twist on the traditional Old Fashioned but uses rum instead of bourbon and was quite tasty.

We enjoyed cigars on the outer deck and enjoyed some tapas. The event ended around 10PM and I decided to make the best of my first night and ventured down to Duval Street and do the traditional “Duval Crawl” hitting some of my favorite live music venues.


The Main Event

The following evening was the main event, so after a day biking around the island, I made my way over to Mallory Square to watch the sunset and then walk over to Rodriguez Cigars of Key West in the Kino Plaza to partake in the festivities.

The intimate event was hosted by Danny DiFabio and his wife Pilar. Attendees were treated to a delectable buffet of gastronomical delights along with cocktails served up by the Papa’s Pilar Rum company. There was outdoor seating and tables for the guests, all of whom had a cigar filled evening sharing stories, meeting old and new friends and of course toasting to the 40 years of Rodriguez Cigars. Danny and Pilar mingled with the guests and made sure everyone was having a good time. The guest list included friends and family along with retailers.


The Renovated Shop

As part of the event, we got to walk around the renovated shop. I have to say, Danny has been working on this for years and since my last visit, I would say he pretty much has accomplished his goal. He has preserved the history of his grandfather’s shop while adding modern touches throughout. The sitting area is comfortable and quiet, and the completion of the history section adds to the allure. Tourists to the shop can take a tour of the history of cigars and the Rodriguez family in Key West. You even get to roll your own cigar.


As long as I have known Danny and Pilar, they have shown me they do everything 1st class, and as a result, Rodriguez Cigars of Key West has grown while keeping a true family feel. Happy Anniversary to You All. Of course, such an anniversary would not be complete without a special cigar to celebrate, and Rodriguez Cigars did not disappoint as Danny introduced the Cuarenta Años (40 Years) at the event. He even raffled off an all-expense paid trip to Nicaragua for one lucky winner. Here’s to another 40 years.

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