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.