key west cigar tour

Rodriguez Cigar Rolling Tour

Highlights:

Use traditional cuban tehniques to manufacture cigars., includes one cigar and a complimentary cuban espresso., tour length is 1 hour and 15 minutes, operating times:, reservation notes:, booth location:, nearest intersection:.

Key West Rebecca

(305) 304-8910

[email protected], rodriguez cigar rolling tour highlights.

75 Minute Tour

Includes One Cigar

Complimentary Cuban espresso

Use traditional Cuban techniques to manufacture cigars.

Take a step back in time and experience an old world family tradition that began in Cuba in 1947.

The Oldest Cigar Company in the Florida Keys. Our master cigar rollers will guide and instruct the full process of manufacturing cigars from start to finish.

Guests will be guided through 4 different stations of preparing wrapping tobacco, constructing the filler, applying the final wrapper and discussing the aging process.

Tours Key West

Key West—America’s Original Cigar City

Tampa’s Cigar City Brewing has won numerous awards and gold medals, and you can order its draft beers at bars all over Key West. While the beers are quite tasty, the irony of this libation is lost on most visitors. While Tampa’s Ybor City, a neighborhood rich in Cuban American traditions, is known as America’s cigar industry epicenter, the earlier version of Cigar City, U.S.A. was not Tampa, but rather the nickname for Key West, the southernmost point in the nation. At its height in 1890, there were at least 80 factories and estimates of cigars hand rolled here run as high as 100 million annually.

In the early 19th century, long before Miami’s rise, Key West was the primary port in southern Florida, the gateway to the nearby Caribbean and Central America, and its docks regularly offloaded shipments of cigars and tobacco from Cuba. In 1831 American businessman William H. Wall started the first cigar factory, importing raw ingredients from Cuba, and employing more than 50 rollers. His soon became one of the smaller operations, and within three decades, widespread labor unrest in Cuba led producers there to look offshore and open factories in Key West, where the cigar industry exploded for the next half century, with many Cuban companies manufacturing Cuban-grown cigars in Florida. One of America’s best-known cigar brands got its humble start here back in 1912, when Cuban emigré Arturo Fuente began making cigars here in 1912.

But Key West’s cigar reign wasn’t a long one. Savage hurricanes destroyed cigar factories, and high labor costs and limited freight connectivity to the rest of a country eager for distribution became impediments to producers. The city of Tampa stepped in with inducements, lower wages and easy access to freight railways, luring away Vincente Ybor, one of the most prominent of the Cuban citizens who had relocated his factory to Key West. Ybor’s operation alone produced as many as ten million cigars yearly, and so many others followed him north that by the 1920s, the cigar industry in Key West had all but vanished. This left a major economic void on the island, and it would be decades before Key West struck gold with tourism, which continues to flourish to this day.

Yet while Tampa may have taken Key West’s cigar industry, it never took away the island’s penchant for good smokes, and in these restrictive times, the island paradise—and the closest place in the U.S. to Cuba— remains one of the most cigar welcoming destinations in the country. As one of America’s most eclectic melting pot communities, it has attracted a very diverse slate of visitors and residents, but if there is a shared trait, it’s an almost roguish libertarian live-and-let-live streak that hearkens back to its pirate days. The island is famously associated with Ernest Hemingway , Jimmy Buffet, and its resident Drag Queens, and has long been a major destination for artists, performers, rebels, anglers, escapists and anyone looking to do their own thing—and whenever possible, do it outdoors. Home to some of the best weather in the nation and omnipresent island breezes, almost all bars, restaurants, and hotels have an open-air component ideal for smokers, and it is telling that Key West’s signature event is the Sunset Festival, a fair-like spectacle of craft stands, food carts and live performers such as jugglers, trapeze artists, acrobats, and musicians, held at sunset every night of the year in seaside Mallory Square, a plaza in the midst of historic Old Town, the main shopping, dining and entertainment district in the northwest corner of the small island (just four by two miles).

Thanks to widespread open container laws, such as those found in New Orleans, just strolling around the streets is one big mobile celebration, and in addition, a lot of the fun of Key West takes place off the island and on the water, as sunset, cocktail and glass bottom cruises, sailing, and especially sportfishing are hugely popular and one of the main reasons people visit. Cigars are not only very welcome here, they are widely available in bars, hotels and retailers, especially in Old Town around the cruise ship port and Duval Street, the island’s busiest commercial thoroughfare. It is hard to walk more than a couple of blocks without passing a cigar retailer (though some should probably be skipped), and there are specialty shops, cigar lounges, many cigar friendly bars and one prominent cigar factory.

“Those cigars they are making are actively preserving an important part of our local history,” said Danny DiFabio, third generation owner of Rodriguez Cigars , pointing at a few of the ten rollers he employs at his small Key West workshop. “When the cigar industry left after the turn of the 19th century, Key West went into economic decline, and we had to reinvent ourselves. We did that first through commercial fishing, and then with tourism. Today we have lost our identity as Cigar City, USA, and are better known for seafood.  It is very important to me to keep an element of domestic cigar making here in Key West. I was born and raised here, it’s my home, and there are a lot of great producers in Nicaragua, but no one else doing it here. It’s my dream to greatly expand our local production.”

DiFabio took over the family business after studying business in college, and while most of the company’s cigars are made in its much larger factory in Nicaragua’s Esteli, where he has another 65 rollers, he wants to bring back the island’s forgotten reputation for cigar excellence. “There really hasn’t been another quality cigar company here since the Fifties. We’re the last one, and because there’s a stigma, we have to try harder, dig deeper, age longer and source better materials. Key West is my home, and I want us to be proud of that.”

He is a passionate cheerleader for this vision, and goes so far as to personally neaten and rearrange the high quality humidors he supplies and stocks at several top cigar friendly Key West hotels including the Reach, Laureate, Gates, and the Casa Marina Waldorf Astoria , generally considered the island’s top luxury resort. He offers twice daily 75-minute hands-on factory tours at Rodriguez Cigars, a workshop cum retail store, and home to two large temperature and humidity-controlled storage rooms. The intimate tours ($35) let visitors try their hand at the start to finish process of hand rolling a cigar, working at four different stations, and include delicious Cuban coffee and a top shelf cigar to go. Rodriguez sits within a hidden shaded courtyard in the heart of Old Town, complete with tables for enjoying a smoke, picnic lunch and beverages, and while they don’t serve liquor, DiFabio is quick to suggest guests bring their own and make it a party, like everything else in Key West. His tours are very popular with visitors on cruise ships, and his passion is contagious, but while Rodriguez Cigars are clearly the local favorite, there are lots of other options.

Open air storefront stands and kiosks selling wide ranges of cigars can be found on the major streets of downtown Key West, though a quick glance can ascertain whether or not they practice quality storage – many do not, lacking humidors and displaying products unwrapped and out in the open in a hot and humid environment where they can absorb lots of moisture. Many Key West bars, especially on boisterous Duval Street, have small bar top humidors, and there are a few first-rate retailers, like Greene Street Cigars, a sizable shop that combines a large walk-in humidor with a bar and smoking lounge. Greene Street holds a beer and wine license, which means no spirits, but it has a sizable selection of local and regional craft beers on draught, a broad range of wines by the glass, and a pleasant bar with stools plus a living room-style lounge area. Smoking is very welcome, but if you prefer there is also a small outside sitting area ideal for sidewalk people watching. It sits just off busy Duval Street in the heart of downtown and carries a couple of hundred selections including most major brands, as well as its own custom label made in Nicaragua.

The best cigar-centric bars around the island are those at the Casa Marina Waldorf Astoria resort, where the actual humidor is within specialty rum bar RUMba, but can be enjoyed at the larger outdoor Sun Sun bar or around the beachfront firepits, and the Rodriguez cigar lounge at Rum Row in the Gates Hotel. This sort of tiki-shack inspired open air poolside bar also serves great food and has live music during evening happy hour. Sunset Pier is one of the most quintessential places on Key West to pop in for a cocktail, occupying a historic long pier that juts into the ocean. A tourism icon, it was destroyed by Hurricane Irma in 2017 and just reopened in 2019. Railside seating on both sides directly overlook the waves, and while no cigars are sold onsite, smoking is welcome, with full and food bar service and often live music. The pier is part of the upscale Ocean Key hotel in a prime location adjacent to Mallory Square, and has long been the preferred island spot for sundowners. Hogfish Grill is another true “island-time” open-air eatery and watering hole, but off the beaten path and more of a local’s favorite, hidden (not very well) in the Safe Harbor marina on Stock Island, an eastern extension of Key West linked to the main island by a short bridge. It’s a thatched roof spot with license plates as décor, straight off the boat local fish on the menu, lots of tropical drinks, shaded picnic tables and a laid-back vibe with frequent live music. There are fishing charters and watersports on site so you can go straight from the sea to festivities.

In addition to cigar friendly spots, Key West is home to several famous bars, most with a purposefully divey ambiance, including Sloppy Joe’s, a now very touristy spot best-known for being Hemingway’s favorite haunt. Captain Tony’s, which occupies the original Sloppy Joe’s location, has an equally colorful history and is also a hotspot on the tourism rota here. There’s more local flavor at the Green Parrot, the island’s oldest saloon, known for great live music.

A large part of Key West’s enduring tourism appeal is its excellent culinary offerings, built around fresh seafood but offering a little bit of everything and lot of high quality. There are many good choices, but for fine dining top picks include Hot Tin Roof (playwright Tennessee Williams was another part time Key West resident) in the Ocean Key hotel, offering first rate service, an excellent seafood driven menu and stellar ocean and sunset views. Latitudes is at the exclusive Sunset Key resort on a private island just off Key West with water taxi service, and the eatery, which has made many national top 100 lists, serves upscale island fare. Santiago’s Bodega is where locals go to celebrate birthdays and anniversaries, a notoriously hard to book spot specializing in small plates or eclectic modern tapas, as varied as they are delicious. Even in this seafood lover’s paradise, the chef-owned Thirsty Mermaid stands out as the prime raw bar take on the genre, and imports top shelf east and west coast oysters to augment the local warm weather varieties, plus creative ceviches and takes on the popular local specialty, conch.

Key West has a lot of middle of the road lodging, but less at the high end. The consensus top two luxury category properties here are the Casa Marina Waldorf Astoria, a large full-service beach resort on over 6-acres with the island’s largest private beach, and Sunset Key Cottages , a private island enclave just off the coast of Old Town. A notch down from these are Ocean Key, which has a great location and multiple dining and drinking outlets, and the Reach , another cigar friendly property that just renovated and reopened as a member of Hilton’s upscale boutique Curio collection. One of the nicest things about Key West is that it is so small that there really are no bad locations, and much of it is walkable, all of it is bikeable, with most hotels supplying loaners. Nothing, including the extremely convenient airport, with non-stops as far as Boston, Newark, Dallas and Chicago, is more than about a 10-minute cab ride.

Key West Insider – tell them how this benefits the subscriber

Call a Fun Coordinator for immediate help 888.667.4386

• Key West Travel Blog
• Uncategorized

Tours Key West offers the most popular tours and attractions in Key West Florida, including Jet Ski Tours, Snorkeling, Parasailing, Dolphin Adventures, Glass Bottom Boat Tours, Sunset Cruises, and so much more. We don't want to sell you just any tour; we want to help you create the exact experience you are looking for on our quirky little tropical island.

Call 305.587.4386 888.667.4386

Book your Key West tours and attractions today

Wild and fun or a bit more upscale or laid back-as Conch travel experts we'll help you plan a trip that's perfect for you.

WE MAKE FUN EASY Call 305.587.4386 888.667.4386

Rodriguez Cigar Factory

Rolling cigars on the island since 1984, Rodriguez Cigars is the oldest cigar company in the Florida Keys.

Sourcing from the finest private plantations the world has to offer, Rodriguez maintains their traditional Cuban manufacturing methods to deliver the top-nodge quality they’re known for.

The Product:

Their collection comprises four unique series, each embodied with its own distinct complexion and character.

Pop in for a private tour of the factory. Owner, Danny DiFabio, will have a Cuban coffee in your one hand and a cigar in the other in no time.

The Key to the Gates Experience

• Orlando Style
• September 7, 2016

When expatriate novelist Ernest Hemingway arrived in Key West in 1928, his items of business included obtaining a spare apartment with his second wife, making a name for himself in the bars among Duval Street, and finishing the painstaking process of perfecting what would become one of America’s greatest novels, A Farewell to Arms. Perhaps your own aspirations of a stay in Key West may not be as legendary as those of the world-travelled writer, but there’s one thing Hemingway and every potential Key West tourist have in common: a thirst for life and a town that can quench it.

Today, you can explore the treasure of Hemingway’s Key West in the modern luxury that now outlines the city; historical buildings now house sights and sounds of Florida’s present, while new shops and experiences still ring of traditions past.

A relaxing getaway to The Gates Hotel provides for a calming atmosphere to enjoy a weekend, or a couple of weeks in beautiful Key West with all of its new and old world charm. Located at the point of entry to Key West, The Gates Hotel is a classic take on the unique culture and stunning beauty of the ocean-laced city. The secluded location only adds to the relaxing flair of the hotel, and trolley rides from the hotel are available to take you straight to Duval street and the center of Key West excitement. Celebrating local art and modern architecture, sophistication finds its way into every square inch of The Gates. The boutique aesthetic of the lobby creates an intimate escape to relax after a day discovering the island. Calming neutral tones and ocean colors captivate guests in a sea of serenity, while modern accents cool off adventures after a long day in the sand and sun. Minimalism is taken to the next level at The Gates as natural elements create a subtle space for guests to escape from the business of daily life, featured in wooden wall design, ethereal flooring, and thoughtful use of graceful hues.

Lazy afternoons in the Florida heat are given an air of elegance at The Gates private pool, an oasis of relaxation not far from the hotel’s dining and drinking options. Take a dip with a drink in hand as quiet hours spent poolside turn into romantic memories of paradise. Just a few steps takes you to Rum Row, The Gates’ well-stocked bar, where you can sip on tastes of Key West such as a variety of rum-soaked cocktails. Also outside, the Blind Pig offers delicious and healthy options on location in a food truck-style experience. Enjoy cuisine inspired by Key West’s eclectic tastes of Caribbean, Cuban, and Floridian culture in the form of small bites and tapas.

In true Key West fashion, The Gates fills each room with work from award winning photographer Jorge de la Torriente of De La Gallery. His work captures the vibrancy of journeying to new destinations of nature and beauty.

Jorge de la Torriente’s work found in The Gates can be enjoyed at De La Gallery, where modern exposition of color meets timeless island culture. The gallery has become a locally-renowned site on Duval Street. This road is a work of art itself, lined with buildings that could tell as many stories as only Hemingway could write. The Hemingway favorite Sloppy Joe’s Bar may be the most famous location on Duval, but many new eateries have raised the bar in Key West. Nine One Five restaurant and wine bar offers an elegant place to enjoy a glass or bottle of beautiful wine, exciting cocktails and delicious cuisine while taking in the excitement of the island’s late nights. If you prefer a more Hemingway-esque drink, your Key West adventure must include a stop to the Key West First Legal Rum Distillery and chat with founder/distiller Paul Menta who embodies quintessential Key West. This distillery combines the best flavors to bring thirsty travelers delicious white rums, made with Florida sugar cane and infused with the flavors of coconut, creme brûlée, and key lime. Their specialty rums are distilled six times filtering out fusel oils that result in headaches to ensure that your drinking experience is unlike any other. The distillery’s rum can also be enjoyed right at The Gates Hotel’s Rum Row Bar.

When Hemingway wasn’t busy writing, if rum was in one hand, it was probable that a cigar was in the other. Keep the traditional Key West experience going with a trip to Rodriguez Cigar Factory, where Danny DiFabio, grandson of the late Angel Rodriguez, now heads up the family’s Key West operation, and where his grandmother, Daniela Rodriguez, still hand rolls hundreds of cigars each day. You can get a taste for exceptional hand-rolled cigars made with cured and aged vintage tobacco leaves in the authentic Cuban style. Founded in Key West in 1984, the factory is the oldest operating cigar manufacturer in town, allowing guests to enjoy a variety of cigars in the cigar garden, a picturesque locale for those craving to breathe in a breath of Hemingway’s Key West.

A few puffs of a hand-rolled cigar might get you in the mood for adventure, and Fury Water Adventures offers catamaran tours fit for whatever you fancy. Chill the night away on a sunset tour, or excite your toes with a trip on Fury’s glass bottom boat as marine life swims right below your view. Perhaps a bit of a closer perspective is what you’re looking for in your ocean adventure. If that’s the case, visit SUP Key West, where you can have an exciting stand up paddleboard tour of the Key West backcountry. Get up close and personal with wildlife as you take a look at tropical fish, sea stars, and jellyfish, as well as different species of aquatic birds. Even learn from the best with customized paddleboard lessons. For seekers of the time-honored tradition of soaking up the adventurous life, there’s no place on the island quite like COAST. Partnering with The Gates Hotel, COAST offers a blend of land and sea in a variety of activities for Key West enthusiasts, from bike tours to art classes. COAST’s Stock Rock ’N Roll bicycle tours are an authentic way to take in the joys of Key West’s laid-back personality. (Just note: It gets very hot in the summer months, so if you can’t take the heat do it when the weather is cooler!) This tour includes a stop at The Key West Botanical Garden and takes travelers to Stock Island. Art lovers can participate in screen printing classes at the COAST Studio, as well as taking in a look and listen of local artists and musicians.

Founder Billy Kearins created COAST in an effort to live an endless summer, riding the lines between land and sea and work and play. He specializes in design projects, builds skateboards and surfboards, and is the head visionary for the classes, projects, and showcases held at COAST. Keeping the back roads alive with adventure, an afternoon at COAST pairs nicely with lunch at Hogfish Bar & Grill, the perfect place to try fresh seafood with seaside views. This spot is a favorite for locals, with outdoor dining and live music in a casual atmosphere.

This is just the beginning of the seemingly endless dining options of Key West. If you like to start your adventures early, make time to indulge in breakfast at Blue Heaven before your explorations begin. Don’t be fooled by the chicken and cats wandering around or the quirky artwork—this restaurant takes its food very seriously. Breakfast favorites such as Eggs Benedict and Shrimp and Grits combine down-home charm with quality flavor worthy to make Blue Heaven a Key West staple. Oysters are on the menu at The Half Shell Raw Bar, where you can get a real old-fashioned taste of the Key West life. Enjoy dinner on the docks as you try seafood that has been plated within hours of being caught.

For larger parties, Catered Affairs is a sophisticated choice for simple and delicious dining. If you’d like to call Key West your destination for corporate functions, family gatherings, or weddings, Catered Affairs brings the beauty of the island and high quality service to your event. Executive Chef Lloyd Gould and Catering Coordinator Amy Lay provide you with the Key West flavors and catering needs you need to throw the best party on the island. After your journey of finding all that Key West has to offer, stop by The Gates’ sister property, 24 North Hotel. Step back in time as you tour this island escape, which is the perfect marriage of Key West and Cuba. It may only be 90 miles away, but 24 North makes the paradise of Cuba seem even closer. Reminisce the days of Hemingway in Key West’s prime as you wander through paradise poolside at 24 North.

From rum and cigars to seafood and the city, there’s an endless bounty for you to discover in Key West. Pack a fedora, take along your loved one, and maybe even a laptop. If we’ve learned anything from Hemingway, there’s much to write about—let alone enjoy—in this Florida getaway town. It’s time for you to experience it yourself.

The usage of this website is reserved for visitors who are adults according to the legal provisions of their respective country.

Please enter your birth date

Remember me

YOUR KEY WEST EXPERTS!

• Historic Walking Tour

The Fuente House – Historic Walking Tour

There are so many connections back to Key West.  Lots of famous people started their lives or careers in Key West.  Arturo Fuente is no exception.  Unless you are into cigars, you may not recognize the name.  Arturo Fuente is the reigning name in premium cigars.  But, how does this gentleman and his name connect to Key West?

From the beginning

Arturo was born in Cuba.  In 1895, at the age of 7 years old he lived in Guiness.  At this time, Cuba’s revolutionaries were fighting the revolution against the Spanish Government.  As a young child, Arturo experienced all of the horrors of war.  He saw the concentration camps created by Spanish General Butcher Weyler to keep the laborers from suppling the insurrectionists.

The Spanish American War began in 1898.  The 10 week war had many notable one-sided victories for the United States.  By 1899, Cuba had won its freedom and was under temporary control of the United States.

Arrives in Key West

With political and economic uncertainties looming, Arturo moved to Key West at the age of 19.  He was reunited with his sisters and other relatives already living in Key West.  Although penniless, he was ready to begin a new adventure.

His home is unmarked by a plaque, but it’s located at 706 Elizabeth street.  From this spot, Arturo would go to work everyday at the A.E. Baez Cigar factory.  It was a small factory known as a “chinchilla”.  These small factories only had a few workers.  But, it was a block away from his home.  At this factory and the Eduardo Hidalgo Gato Cigar factory , Arturo perfected his craft of rolling cigars.

During this time in Key West, Arturo could walk to work and pass small businesses such as coffee shops, restaurants, laundries and grocery stores all owned by Cuban immigrants.

Moves North

In 1912, after many years of apprenticeship, Arturo moved north to Ybor City, Florida.  Located in Tampa, this area was known for its cigar factories.  At the age of 24, Arturo opened his own factory and began to manufacture cigars.  In 1924, the company experienced a devastating fire and closed its doors for 24 years.  The company reopened as a local and limited company in 1946.  Arturo’s youngest son, Carlos took over in 1958.

After the Cuban embargo, the Arturo Fuente company steadily grew.  Today, the company manufactures 30 million cigars and has production facilitates in the Dominican Republic.  In addition to cigars, the company also offers a brand of coffee and high-end watches.

As you walk through the streets of Key West, you cannot help but notice all of the surrounding history.  Take time to visit the stops along the Historic Walking Tour.  You never know what you might see!

Related Posts

Carriage Barn an Unexpected Find in Key West

At 1128 Olivia, between White and Frances Street stands an interesting building.  It looks like a barn, and, in fact,...

Rock House Gallery a Gothic Inspired location

Located at 330 Julia Street is the Rock House Gallery.  It is what was originally the Saint Stephen Methodist...

Island City House the Oldest Guesthouse in Key West

Although Island City House may be the oldest guesthouse in Key West, it is still grand, beautiful and a wonderful...

Lifestyle: Rodriguez Cigars Key West – A Revisit

Back in November, for my 62nd birthday, I decided I needed a laid back, unwinding, relaxing vacation after a long year that had some seriously stressing moments. When this happens, my favorite go to spot is the Florida Keys, especially the city of Key West. I have been there well over 25 times and I tend to know America’s Caribbean Island like the back of my hand. Back in the day, I would spend days and nights finding the newest or oldest bar on the island but now as I am older, I have come to appreciate the island for what it is, a relaxing vacation spot filled with great American history, folklore, and amazing food.

Of course, as an avid cigar enthusiast, I enjoy my cigar stash also. I like to sit on a deck or patio of the hotel or resort and people watch. But when it comes to visiting a cigar shop on the Island – there is no better place than Rodriguez Cigars. It is the oldest running cigar factory on the Island and their craft is second to none. Founded in 1984, the shop has passed down within the family from grandfather to grandson (Danny DiFabio). It is a family owned business that began in Cuba in 1947 where Danny’s grandfather (Angel) and family, grew and harvested tobacco on the family plantation, La Finca de Carmencita, located in the Las Villas province of Cuba. Of course this was before the Castro run government nationalized the industry. The family found their way over to the United States and settled in Key West, Florida in 1971 and eventually opened the Rodriguez Cigar Co. and factory in 1984.

I remember visiting this quaint Key West cigar shop back in the late 1980’s and 1990’s and enjoyed watching Danny’s grandmother (Daniela) rolling panatelas. Angel tended to the shop and greeted those who entered with the same infectious smile that Danny has now. Due to work and family commitments my visits to the island slowed down but about a decade ago, I once again made treks to the island and visit the shop – that his when I met Danny and learned of his grandfathers passing.

Danny explained that he took over the business after graduating college with a business degree. It was not his first choice of a career but with the passing of his grandfather, he knew in his heart that this was what he needed to do in order to keep the family legacy alive. With Danny at the helm, he made numerous changes over the past decade. He started with a collaboration with Guillermo Peña, a master cigar blender who immigrated from Cuba. Guillermo opened a small factory in 2009 in Miami and now owns and operates the La Perla Cigar Factory in Nicaragua. This collaboration led to the first Rodriguez cigar not produced in Key West. Danny named the blend, the Series 84, paying tribute to the year his family started operations in Key West and to always remember his grandfather. Born out of that collaboration, Danny and Guillermo have created a full line of highly acclaimed blends.

The Expansion of Rodriguez Cigars

Danny went on to build out an aging and storage room on the second floor of the shop so he could maintain inventory and subsequently launched a website where consumers can order cigars directly from the store. He slowly and meticulously formed relationships with about 100 shops in the USA that carry the Rodriguez Cigars line. Working with local merchants on Key West, he set up humidors in some of the hotels and resorts on the island to further build brand awareness and even forged a relationship with the Papa’s Pilar rum factory to create rum flavored cigars using the company’s rum barrels.

If that wasn’t enough, Danny acquired the building next door and expanded the shop, both on the ground floor and the second floor aging room, and rearranged it, increased the number of rolling tables, and added a seating area to greet customers and conduct business. With the shop and factory laid out to his liking he made his next business move and started the Rodriguez Cigars Key West factory tour.

The tour costs $35.00/person and lasts about 1 hour and 15 minutes. It is designed to guide and educate guests through 4 different stations of preparing wrapping tobacco, constructing the filler, applying the final wrapper and explaining the aging process. The process highlights traditional Cuban techniques to manufacture cig ars and includes one cigar and a complimentary Cuban espresso. There is even a short movie that tells the Rodriguez family story.

During my visit, Danny invited me to join him on the tour and I have to say, this is a must for any cigar enthusiast who visits Key West.

History of Cigars in Key West and Growth of Rodriguez Cigars

The tour starts with a discussion of Key West cigar history starting back in 1813. The history is informative and well presented. Danny explains how Martinez Ybor, a Spanish entrepreneur, who first became a noted industrialist and cigar manufacturer in Cuba, then Key West, and finally Tampa, Florida. Yes that is how Ybor city got its name. While his business prospered, conflict between Spanish and Cuban workers, labor unrest, and the difficulty of transportation to and from the island city of Key West eventually led Martinez Ybor to decide that he should again relocate his business.

Cigar Leaf and Primings

The tour then goes into how the plants are grown, harvested, cured, and aged. Danny explains the different primings and hands you a stack of each priming – ligero, seco, viso – and has you stack them to the height that each leaf would be on the plant. This gives you an appreciation of how tall the plant is and also the harvesting process as he explains that the last leaves to be primed is the ligero, the top leaves of the plant. You can’t help but smell the aroma coming off those aged leaves you are holiding.

The Rodriguez Cigars Story

The next stop is a watching a short film presented on the front wall off the shop. As you watch the story of the Rodriquez family and the growth of the Key West factory and shop, you are served some Café Cubano, a most delicious sweet cup of Cuban espresso. Once you have some of this, you only want more, and once you have it made properly there is little comparison.

Rolling Cigars

A factory tour would not be complete without learning how to roll your own cigar. Danny sits down at a rolling table and demonstrates how leaves are bunched together to create the filler blend and then applies the binder leaf. The unfinished cigars are then set in a mold and pressed to shape. Guests are taught, hands on, how to use the press. Once the cigars are pressed the molds, they are removed and the each cigar has a wrapper applied. Danny shows the guests how to apply the wrapper and then each guest tries their hand at the age old craft. It is not as easy as it looks but they seem to get through it with some guidance from the master.

Part of the tell is about the beauty and elasticity of the wrapper leaf and how you cut it with a chaveta, the cigar makers prize tool to trim the leaf. There is a special technique to trim and then properly apply the leaf to the cigar. Once finished you apply the cap and you have your own fresh rolled cigar! Of course it is not recommended to smoke it right away, but rather take it home and let it rest so that the blend of leaf can marry together over time and the moisture has a chance to balance out.

One of the other experiences you will have is smelling the aroma of a piece of rolled leaf. This is how blenders can sense the flavor characteristic of each leaf. Danny pint out that you should not put you nose right up to the smoldering leaf. Instead let the smoke expand in the air near you and then smell it, you will have a better grasp of the flavors that leaf produces when ignited.

The Storage and Aging Room

As noted earlier, Danny built out a large storage and aging room on the second floor. The first thing you notice is the much cooler temperature in the room. There are stacks of boxed cigars resting on shelves to be delivered to shops and customers around the countr. As this stop is the completion of the tour, Danny even presented each guest with a special cigar that is not sold on the market. It is known as the 1813, a special cigar that celebrates the year Key West started making cigars.

Danny will tell you:

“With over 67 years of being in the tobacco industry our primary mission still, and will always remains the same…To deliver a premium, consistent product enriched with the Cuban Heritage.”

I can attest that having been a fan of Rodriguez Cigars since the late 1980’s, and having the pleasure of knowing his Grandfather and Grandmother, Danny has made the family proud in the expansion of the brand and the shop/factory. While there may be other shops on the island, nothing compares to the experience you will have at Rodriguez Cigars Key West. The personal attention and passion for the craft is second to none and even the folks that I took the tour with were happy with the education they received during the 75 minute tour. They even purchased some boxes of Rodriguez cigars for themselves and to give as gifts to family and friends up north as a little part of Key West.

If you are planning to visit Key West anytime soon, add the Rodriguez Cigars Factory Tour to you list of fun things to do on the island.

Two tours a day are held Monday through Saturday:

• Morning Tour : 10:30 AM
• Afternoon Tou r: 1:30 PM

You can book a tour directly from the company’s website here

Rodriguez Cigars Location, Contact, and Hours of Operation

Rodriguez Cigars Key West is located at 113 Fitzpatrick St Key West, FL 33040

• The Store is open 7 days a week from 9:30 Am to 4:30 PM

Phone : 305-296-9167

Email : [email protected]

Website : https://rodriguezcigarskeywest.com/

Facebook : @rodriguez.cigars 

Instagram : rodriguezcigars

Twitter: @Rodriguezcigars

Share this:

2 thoughts on “ lifestyle: rodriguez cigars key west – a revisit ”.

that is cheryl & i had fun during that time nice to meet you jimmy

It was such a pleasure to be there that day and watch you all roll cigars I hope you’re enjoying reading my blog.

Boston Jimmie

Comments are closed.

Hand Rolled

Talmaege is our Super Premium line of cigars named for our long-time lead roller: Talmaege Culmer

Since 1963 The oldest in Key West A glimpse at our Factory where our Cigars are rolled today.

is the Conch Republic

Skilled Rollers

Featured products.

Cuban Split - 10pak Free Shipping

Jamaican Rhum - 10 Count Shipping Included

Jamaican Vanilla 10 Count Shipping Included

Cuban Split - Corona Corta - 25 Count Shipping Included

New customer.

Create an account with us and you'll be able to:

• Check out faster
• Save multiple shipping addresses
• Access your order history
• Track new orders
• Save items to your wish list

Forgot Password

Fill in your email below to request a new password. An email will be sent to the address below containing a link to verify your email address.

Cigar Aficionado

Key West—America’s Original Cigar City

Tampa’s Cigar City Brewing has won numerous awards and gold medals, and you can order its draft beers at bars all over Key West. While the beers are quite tasty, the irony of this libation is lost on most visitors. While Tampa’s Ybor City, a neighborhood rich in Cuban American traditions, is known as America’s cigar industry epicenter, the earlier version of Cigar City, U.S.A. was not Tampa, but rather the nickname for Key West, the southernmost point in the nation. At its height in 1890, there were at least 80 factories and estimates of cigars hand rolled here run as high as 100 million annually.

In the early 19th century, long before Miami’s rise, Key West was the primary port in southern Florida, the gateway to the nearby Caribbean and Central America, and its docks regularly offloaded shipments of cigars and tobacco from Cuba. In 1831 American businessman William H. Wall started the first cigar factory, importing raw ingredients from Cuba, and employing more than 50 rollers. His soon became one of the smaller operations, and within three decades, widespread labor unrest in Cuba led producers there to look offshore and open factories in Key West, where the cigar industry exploded for the next half century, with many Cuban companies manufacturing Cuban-grown cigars in Florida. One of America’s best-known cigar brands got its humble start here back in 1912, when Cuban emigré Arturo Fuente began making cigars here in 1912.

But Key West’s cigar reign wasn’t a long one. Savage hurricanes destroyed cigar factories, and high labor costs and limited freight connectivity to the rest of a country eager for distribution became impediments to producers. The city of Tampa stepped in with inducements, lower wages and easy access to freight railways, luring away Vincente Ybor, one of the most prominent of the Cuban citizens who had relocated his factory to Key West. Ybor’s operation alone produced as many as ten million cigars yearly, and so many others followed him north that by the 1920s, the cigar industry in Key West had all but vanished. This left a major economic void on the island, and it would be decades before Key West struck gold with tourism, which continues to flourish to this day.

Yet while Tampa may have taken Key West’s cigar industry, it never took away the island’s penchant for good smokes, and in these restrictive times, the island paradise—and the closest place in the U.S. to Cuba— remains one of the most cigar welcoming destinations in the country. As one of America’s most eclectic melting pot communities, it has attracted a very diverse slate of visitors and residents, but if there is a shared trait, it’s an almost roguish libertarian live-and-let-live streak that hearkens back to its pirate days. The island is famously associated with Ernest Hemingway , Jimmy Buffet, and its resident Drag Queens, and has long been a major destination for artists, performers, rebels, anglers, escapists and anyone looking to do their own thing—and whenever possible, do it outdoors. Home to some of the best weather in the nation and omnipresent island breezes, almost all bars, restaurants, and hotels have an open-air component ideal for smokers, and it is telling that Key West’s signature event is the Sunset Festival, a fair-like spectacle of craft stands, food carts and live performers such as jugglers, trapeze artists, acrobats, and musicians, held at sunset every night of the year in seaside Mallory Square, a plaza in the midst of historic Old Town, the main shopping, dining and entertainment district in the northwest corner of the small island (just four by two miles).

Thanks to widespread open container laws, such as those found in New Orleans, just strolling around the streets is one big mobile celebration, and in addition, a lot of the fun of Key West takes place off the island and on the water, as sunset, cocktail and glass bottom cruises, sailing, and especially sportfishing are hugely popular and one of the main reasons people visit. Cigars are not only very welcome here, they are widely available in bars, hotels and retailers, especially in Old Town around the cruise ship port and Duval Street, the island’s busiest commercial thoroughfare. It is hard to walk more than a couple of blocks without passing a cigar retailer (though some should probably be skipped), and there are specialty shops, cigar lounges, many cigar friendly bars and one prominent cigar factory. 

“Those cigars they are making are actively preserving an important part of our local history,” said Danny DiFabio, third generation owner of Rodriguez Cigars , pointing at a few of the ten rollers he employs at his small Key West workshop. “When the cigar industry left after the turn of the 19th century, Key West went into economic decline, and we had to reinvent ourselves. We did that first through commercial fishing, and then with tourism. Today we have lost our identity as Cigar City, USA, and are better known for seafood.  It is very important to me to keep an element of domestic cigar making here in Key West. I was born and raised here, it’s my home, and there are a lot of great producers in Nicaragua, but no one else doing it here. It’s my dream to greatly expand our local production.”

DiFabio took over the family business after studying business in college, and while most of the company’s cigars are made in its much larger factory in Nicaragua’s Esteli, where he has another 65 rollers, he wants to bring back the island’s forgotten reputation for cigar excellence. “There really hasn’t been another quality cigar company here since the Fifties. We’re the last one, and because there’s a stigma, we have to try harder, dig deeper, age longer and source better materials. Key West is my home, and I want us to be proud of that.” 

He is a passionate cheerleader for this vision, and goes so far as to personally neaten and rearrange the high quality humidors he supplies and stocks at several top cigar friendly Key West hotels including the Reach, Laureate, Gates, and the Casa Marina Waldorf Astoria , generally considered the island’s top luxury resort. He offers twice daily 75-minute hands-on factory tours at Rodriguez Cigars, a workshop cum retail store, and home to two large temperature and humidity-controlled storage rooms. The intimate tours ($35) let visitors try their hand at the start to finish process of hand rolling a cigar, working at four different stations, and include delicious Cuban coffee and a top shelf cigar to go. Rodriguez sits within a hidden shaded courtyard in the heart of Old Town, complete with tables for enjoying a smoke, picnic lunch and beverages, and while they don’t serve liquor, DiFabio is quick to suggest guests bring their own and make it a party, like everything else in Key West. His tours are very popular with visitors on cruise ships, and his passion is contagious, but while Rodriguez Cigars are clearly the local favorite, there are lots of other options. 

Open air storefront stands and kiosks selling wide ranges of cigars can be found on the major streets of downtown Key West, though a quick glance can ascertain whether or not they practice quality storage – many do not, lacking humidors and displaying products unwrapped and out in the open in a hot and humid environment where they can absorb lots of moisture. Many Key West bars, especially on boisterous Duval Street, have small bar top humidors, and there are a few first-rate retailers, like Greene Street Cigars, a sizable shop that combines a large walk-in humidor with a bar and smoking lounge. Greene Street holds a beer and wine license, which means no spirits, but it has a sizable selection of local and regional craft beers on draught, a broad range of wines by the glass, and a pleasant bar with stools plus a living room-style lounge area. Smoking is very welcome, but if you prefer there is also a small outside sitting area ideal for sidewalk people watching. It sits just off busy Duval Street in the heart of downtown and carries a couple of hundred selections including most major brands, as well as its own custom label made in Nicaragua. 

The best cigar-centric bars around the island are those at the Casa Marina Waldorf Astoria resort, where the actual humidor is within specialty rum bar RUMba, but can be enjoyed at the larger outdoor Sun Sun bar or around the beachfront firepits, and the Rodriguez cigar lounge at Rum Row in the Gates Hotel. This sort of tiki-shack inspired open air poolside bar also serves great food and has live music during evening happy hour. Sunset Pier is one of the most quintessential places on Key West to pop in for a cocktail, occupying a historic long pier that juts into the ocean. A tourism icon, it was destroyed by Hurricane Irma in 2017 and just reopened in 2019. Railside seating on both sides directly overlook the waves, and while no cigars are sold onsite, smoking is welcome, with full and food bar service and often live music. The pier is part of the upscale Ocean Key hotel in a prime location adjacent to Mallory Square, and has long been the preferred island spot for sundowners. Hogfish Grill is another true “island-time” open-air eatery and watering hole, but off the beaten path and more of a local’s favorite, hidden (not very well) in the Safe Harbor marina on Stock Island, an eastern extension of Key West linked to the main island by a short bridge. It’s a thatched roof spot with license plates as décor, straight off the boat local fish on the menu, lots of tropical drinks, shaded picnic tables and a laid-back vibe with frequent live music. There are fishing charters and watersports on site so you can go straight from the sea to festivities.

In addition to cigar friendly spots, Key West is home to several famous bars, most with a purposefully divey ambiance, including Sloppy Joe’s, a now very touristy spot best-known for being Hemingway’s favorite haunt. Captain Tony’s, which occupies the original Sloppy Joe’s location, has an equally colorful history and is also a hotspot on the tourism rota here. There’s more local flavor at the Green Parrot, the island’s oldest saloon, known for great live music.

A large part of Key West’s enduring tourism appeal is its excellent culinary offerings, built around fresh seafood but offering a little bit of everything and lot of high quality. There are many good choices, but for fine dining top picks include Hot Tin Roof (playwright Tennessee Williams was another part time Key West resident) in the Ocean Key hotel, offering first rate service, an excellent seafood driven menu and stellar ocean and sunset views. Latitudes is at the exclusive Sunset Key resort on a private island just off Key West with water taxi service, and the eatery, which has made many national top 100 lists, serves upscale island fare. Santiago’s Bodega is where locals go to celebrate birthdays and anniversaries, a notoriously hard to book spot specializing in small plates or eclectic modern tapas, as varied as they are delicious. Even in this seafood lover’s paradise, the chef-owned Thirsty Mermaid stands out as the prime raw bar take on the genre, and imports top shelf east and west coast oysters to augment the local warm weather varieties, plus creative ceviches and takes on the popular local specialty, conch.

Key West has a lot of middle of the road lodging, but less at the high end. The consensus top two luxury category properties here are the Casa Marina Waldorf Astoria, a large full-service beach resort on over 6-acres with the island’s largest private beach, and Sunset Key Cottages , a private island enclave just off the coast of Old Town. A notch down from these are Ocean Key, which has a great location and multiple dining and drinking outlets, and the Reach , another cigar friendly property that just renovated and reopened as a member of Hilton’s upscale boutique Curio collection. One of the nicest things about Key West is that it is so small that there really are no bad locations, and much of it is walkable, all of it is bikeable, with most hotels supplying loaners. Nothing, including the extremely convenient airport, with non-stops as far as Boston, Newark, Dallas and Chicago, is more than about a 10-minute cab ride.

More in Where to Smoke

Another luciano cigars branded lounge opens in texas.

Industrial Cigar Co., a family-owned cigar lounge in Frisco, Texas, has partnered with Luciano …

Oliva Opens New Cigar Lounge In Germany

Fans of Oliva Cigars have a new location to light up their favorite smokes.

Club Macanudo Makes Its Way To Margaritaville

The Bayou State’s lesser-known Bossier City is home to the newest Club Macanudo, located at the …

The Hardy Room, Nemacolin Resort, Farmington, Pennsylvania

The cigar lounge has three parts, a retail cigar and accessory shop with separate entrance, connected …

Le Fumoir, Ciragan Palace, Istanbul, Turkey

The entire property is fresh off a top to bottom renovation and even better than before—including a …

Byron Lounge Opens In Nashville Cigar Bar

A new Byron cigar lounge has been added to a freshly remodeled cigar bar known as The Ariston, …

Virgin Voyages' guide to Cruise Key West

A haven for artists and sunset-seekers alike, the only poetic rival to the writers who called Key West home is the geography itself.

It’s all a breeze in the keys

More than its pirate past and raucous Duval Street parties (although, to be fair, those are worth the hype), Key West is home to an ever-evolving community of boundary-pushing artists and dedicated preservationists—lined with pastel-colored houses and nights spent toasting sunsets so incredible they inspire some of the world’s most sacred art.

What to see and do on the island

The Shore Things, the tour things and Hemingway’s fur things

Dolphin Watch and Wildlife Snorkel

A dolphin-watching and wildlife snorkeling trip

Key West Rum & Cigar Tasting Tour

A tour of the cigar and rum industry in Key West

The Duval Crawl: Key West's Pub Crawl

Pub crawl down Duval Street at the liveliest bars

Key West Rum and Cigar Tasting Tour

The duval crawl: key west's pub crawl, we have even more in our curated catalog., named by spanish settlers — english speakers heard, “key west” instead., shore things.

Parasail the Painted Island Skies

Float through the air as one of the 12-passenger parasailing boats glides you past sights that can only be seen from the air. As you parasail, take a look below to spot dolphins playing in the surf, or colorful tropical birds flying past.

When the sun sets in Key West… you’ll know. And not just because a myriad of artists from Jimmy Buffet to Judy Blume will make art inspired by the island’s evening end. You’ll know because the sky lights up like fire—tangerine and gold stretching far and wide across the Caribbean sea as you pull away from the dock. Setting on a day spent in a place that goes far beyond a bachelor and bachelorette party destination—where the best of New Orleans and Nantucket meet in the Caribbean to create a little island with a very big personality.

Set Sail the Virgin Way

Set sail the Virgin way and find a new approach to cruise vacations. Select this special itinerary and let's sail.

Fire & sunset soirées.

Painted skies in the Florida Keys

Be the first to get our exclusive deals + onboard happenings

Oops, something went wrong. Please try again or visit our Contact Us page. You can also:

• Check you've typed your email address correctly.
• Make sure you've checked the signup box.

Key West Cigar Club

Top ways to experience nearby attractions

Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.

Also popular with travelers

Key West Cigar Club - All You Need to Know BEFORE You Go (2024)

• (0.03 mi) Old Town Manor
• (0.04 mi) Casa 325
• (0.08 mi) Artist House
• (0.07 mi) Rose Lane Villas
• (0.06 mi) Simonton Court Historic Inn and Cottages
• (0.00 mi) Wendy's
• (0.01 mi) Wicked Lick
• (0.02 mi) Halo Rooftop Lounge
• (0.03 mi) Wendy's
• (0.03 mi) The Flaming Buoy Filet Co.

Festivals & Events

63rd annual key west home tours.

When: December 28 - March 18, 2023

Where: The Oldest House Museum, 322 Duval St, Key West, FL 33040

The Old Island Restoration Foundation (OIRF) is proud to present the 63rd Annual Key West Home Tours! This self-guided tour is the perfect opportunity to explore some of the most beautiful 19th and 20th century residences on the island, learn fascinating history, and enjoy fine art collections and antiques.

This four-month tour starts December and ends March, kicking off with homes festively dressed for the holidays. Tours are scheduled for each month, Jan. 13-14, Feb. 17-18, and March 17-18, giving locals and visitors alike a chance to peek inside some of the most beautiful homes on the island.

The Oldest House Museum located at 322 Duval Street offers tickets for purchase online at OIRF.org or in person. It is important to note that tickets purchased in advance are discounted at $45 for members and $55 for non-members, while tickets purchased at the door are $60. With each tour, participants will be welcomed into the private homes of some of Key West's residents and receive an overview from docents of the style and historical features of the home.

Key West's renovated cigar-makers' cottages, historical restorations, and lavish Victorian mansions create an intriguing architectural fusion. There are believed to be 3,000 structures in the US's largest predominantly wooden historic district in Key West. By attending the Home Tours, visitors can unlock the mystery of what's behind many of Key West's most intriguing front doors.

The proceeds from ticket sales will help support the ongoing mission of OIRF to promote the restoration and preservation of Key West's historically significant buildings. Don't miss out on the opportunity to be a part of this 63 year-old tradition and celebrate the unique architecture, culture and history of Key West!