A walking tour reveals 19th-century Key West, or Cayo Hueso.

By Rafael Lima

Early morning on Duval Street in Key West, and the sidewalk traffic is thriving.

The "Cuban Leaf Cigar Factory," as the hand-carved sign announces, is a single man in a small shop. He is perhaps 70 and shirtless in the summer heat. His cropped white hair contrasts with his weathered brown skin as he bends over a sweat-stained wooden table. He rolls the cigars seemingly in time with the scratchy salsa – Celia Cruz's "Azucar" – leaking from a small boom box.

"How long have you been rolling cigars?"

His eyes crinkle into slits and he tallies the years in his head. "It's 55 years now." His fingers are on automatic, manipulating the leaves.

"Are you Cuban?"

He smiles and nods. "Cuban, but born here. I'm a conch." There is just a hint of a Spanish accent. "My father and my grandfather were both conchs and cigar rollers." Several chickens cluck at his feet, then scurry outside, dodging the tourists.

"I'm doing a story on the Cuban heritage of Key West."

The torcedor stops his work. "Then you must start at the San Carlos Institute." He points and I follow his long, bony finger to a Colonial-style building a half-block away.

"If Cuba had an embassy in the United States, the San Carlos would be it... It is Cuba. It is Havana."

Focusing in the morning sun, I can see the Cuban national seal carved into the façade.

"Go to the end of Duval to the LateDa guest house and look at the veranda where Jose Martí gave speeches to the revolutionaries. Visit the Gato cigar factory and the monument to the Ten Years War and the memorial to the sailors of the USS Maine. It blew up in Havana and the U.S. went to war."

He fans his hand across Duval Street, then smiles and resumes his rolling.

What is your name? I asked.

"Pablo" he says. "Only Pablo." And he disappeared into a backroom.

'Clear Havana'

"Pablo" is a descendant of the thousands of Cubans who fled the revolt against Spain in 1868. Cubans migrated to Key West by the hundreds and brought the Havana cigar business with them. These immigrant cigar makers imported tobacco from Cuba and began rolling local cigars with Cuban tobacco. Their product was called "Clear Havana" since little tax was demanded by Spain for raw leaf exports compared to rolled cigars.

Cigars became big business and Spanish became the unofficial second language of the island. In 1870, the newspaper El Republicano was printed locally in Spanish. Cuba's influence on the island grew as more cigar workers arrived. In 1875, Carlos Cespedes, a Cuban national who could speak only Spanish, was elected mayor.

The San Carlos

The San Carlos was opened on Nov. 11, 1871, in a small wooden building on Anne Street near Key West's old city hall. The institute was named after Cuba's Seminario San Carlos, a place of higher learning renowned for its academic excellence.

The San Carlos is the cradle of Cuba's independence movement. Here, Jose Martí united the exile community in 1892 to launch the final phase of his campaign. Martí so loved the San Carlos that he called it "La Casa Cuba."

The institute's exhibit rooms showcase permanent and traveling exhibits primarily focusing on Cuban history and the Cuban-American community in Florida. Visitors can browse historical texts and admire Cuban art from the turn of the 20th century.

Wooden Indian

It's time for lunch. On a side street off busy Duval, the sidewalks are lined with Conch houses and bougainvillea. El Siboney is in the heart of Old Town between Catherine and Margaret streets.

The regulars here are local residents and customers in-the-know. A large wooden Indian (used occasionally as a Cuban symbol for the supernatural) stares at me as my lunch is served – arroz con pollo, a typical Cuban dish, served with fried bananas and a beer.

As the waiter, also Cuban, pours the beer into a frosty mug, I ask: "How far to the Key West cemetery?"

'Remember the Maine'

Why visit a cemetery on vacation? Because every destination has an invisible history. Here in Key West, Cuban, American and Spanish history have a confluence. Events that radiated from this island tipped the United States on a course toward becoming a world power.

Past a rusting wrought-iron gate, the weathered headstones are shaded by palm trees. A bronze statue of a sailor holding an oar looks off at a far horizon. I imagine he's straining his eyes towards Cuba.

In 1898, the battleship Maine and the sailors under these gravestones made Key West home. A year later, President William McKinley ordered the Maine to sail to Cuba to flex America's military might in support of American business interests in that country. On Feb. 15, 1898, as the ship sat in Havana Harbor, an explosion tore apart the ship and killed 266 of its crew.

Many of the surviving crew were badly burned and returned to Key West to be cared for by the nuns at Mary Immaculate convent. The dead were also returned and today lie buried here.

The United States' subsequent war with Spain won independence from Spain for many of her island possessions, including Cuba, Puerto Rico and the Philippines.

Mallory Square

It is early evening now as I approach a three-story red brick building near the Gulf of Mexico.

The Custom House, built in 1891, is one of Key West's premier historical attractions, at various times home to federal courts, U.S. Customs, the Lighthouse Service and the Post Office. During World War I, Thomas Edison worked here throughout his stay in Key West, at that time Florida's most populous and important seaport.

Situated adjacent to an 1820s naval base, the Custom House was the site of the inquiry into the sinking of the Maine. From a second-story room facing the Gulf of Mexico, some say, the United States decided to go to war with the cry: "Remember the Maine!"

Today, three floors of Key West Cuban heritage include remnants of the battleship Maine and mementos from Edison and the heyday of Pan-American airways' Havana/Key West routes.

Meson De Pepe

Steps from the Custom House is another brick building, a wreckers' warehouse that dates to the 1800s. Today, the restored building houses a Cuban eatery called El Meson De Pepe.

The fragrance of roasting onions, green peppers and saffron greets visitors now. Through the dining room and a back door is a rear courtyard, its seawall flush against the Gulf of Mexico.

At the water's edge, Havana is closer than Miami. That proximity is a reminder of the history of Cayo Hueso – of cafe con leche and arroz con pollo and maduro cigars, of revolution, exodus and international conflict.  

Key West Cigar Shops

Cigar City USA

Located at 410 Wall St., Mallory Square, this shop features art and collectibles as well as fine cigars.

Conch Republic Cigars

Located in the alley next to Ricks Complex on Duval Street.

Cuban Leaf Cigar Factory

Located at 310 Duval St. across from the Hard Rock. Even if you don't want to buy a cigar, this is a great place to stop and watch someone rolling a cigar in the traditional Cuban methods.

Dominican Republic Cigar Shop

925 Duval St.

Garcia Cigar

629 Duval St.

Island Cigar Factory

1100, 218 and 221 Duval St. and 501 Greene St. This factory makes more than 70 types of cigars as well as custom cedar wood boxes.

Key West Havana Cigar Company

Located at the Speakeasy Inn at 1117 Duval St. This store has a walk-in cedar humidor. Enjoy your cigar while sitting on a comfortable couch in the shop surrounded by old art.

King's Treasure's Cigars

Located on the 200 block of Duval Street, this is a high-end shop that also carries pipes and pipe tobacco.

Land's End Cigars

Located near Turtle Kraals nestled amongst a bunch of little shops.

Old Key West Cigar Factory

Located on "Cigar Alley," a.k.a. "Pirate's Alley," this is a cigar shop filled with all types of traditional cigar products from days of old.

The Original Key West Cigar Factory

Located at 1200 4th St., Suite 134, but their cigars are actually sold at Cork and Stogie, 1218 Duval St.

Rodriguez Cigar Factory

113 Fitzpatrick St. Owned by Cuban cigar rollers.


Terrace of La te Da historic hotel in Key West

Jose Martí often spoke from this terrace of the La-te-da.

- San Carlos Institute

A memorial to sailors at Key West cemetery

At Key West cemetery, a memorial to sailors who died in the USS Maine explosion in Havana harbor in 1898.

- San Carlos Institute

The Gato Cigar Company building

The Gato Cigar Company building is now an office complex.

- San Carlos Institute

Jose Martí statue in Bayview Park

Cuban independence leader Jose Martí, memorialized with a statue in Bayview Park, united the exile community in the late 1800s from his headquarters at the San Carlos Institute.

- San Carlos Institute